Steroids and Derivatives

<p>Calcipotriol EP Impurity H is an impurity found in calcipotriol EP. It is a metabolite of calcipotriol EP, which is the active ingredient in Dovonex. Calcipotriol EP Impurity H can be detected by HPLC with a retention time of 11.5 minutes and its purity can be determined by UV spectroscopy at 254 nm with a purity of &gt;98%. Calcipotriol EP Impurity H can also be synthesized from natural or synthetic sources.</p>

<p>Soluble in Chloroform &amp; in Methanol Confirmed<br>Insoluble in Wate</p>

<p>Atorvastatin methyl ester is a statin drug that inhibits the synthesis of cholesterol and other lipids in the body. It is used to reduce high levels of low-density lipoprotein (LDL) cholesterol, which may lead to heart disease or stroke. Atorvastatin methyl ester has been shown to be effective in reducing the uptake of LDL cholesterol into cells by preventing the formation of LDL particles. This drug also decreases the production of biphosphate-containing phospholipids, which are essential for dendritic cell maturation. The crystalline polymorphs have been characterized by X-ray diffraction and microscopy. Impurities can be detected using ultraviolet spectroscopy, infrared spectroscopy, or nuclear magnetic resonance spectroscopy.</p>

<p>Difluoro atorvastatin is a filtrate of atorvastatin, which is a cholesterol-lowering drug. It is synthesized by reacting butyric acid with atorvastatin in an organic solvent. The reaction solution was filtered to remove impurities and then purified by liquid chromatography. The product was characterized by diffraction and LC-MS analysis. Difluoro atorvastatin has a high purity and is suitable for further use in the preparation of pharmaceuticals.</p>

<p>Atorvastatin epoxydione impurity (EPI) is a heptanoic, hydrate, diastereoisomer, racemic mixture, enantiomer and impurity of Atorvastatin. The EPI has been minimized in the formulation process by using a novel synthesis route that employs a chiral pyrrole derivative as an intermediate. This minimization has allowed for the elimination of the tautomer and other impurities present in the original compound.</p>

<p>Calcipotriol EP Impurity E is a synthetic impurity that is found in the calcipotriol EP API. Calcipotriol EP Impurity E is an impurity standard for HPLC and can be used in drug development, research and development, and pharmacopoeia. It has been shown to have no significant effect on the pharmacological activity of calcipotriol EP.</p>

<p>O-Methyl atorvastatin calcium is a drug product that is an HPLC standard. It is a natural metabolite of atorvastatin, which is synthesized by cytochrome P450 3A4 in the liver. O-Methyl atorvastatin calcium has been shown to be an impurity in some batches of atorvastatin calcium. It has been observed to have pharmacological effects similar to those of atorvastatin. O-Methyl atorvastatin calcium has been used as a research and development (R&amp;D) tool for studies on the metabolism of drugs, including its own synthesis and the study of the effect on other drugs such as amiodarone.</p>

<p>Atorvastatin lactone is a prodrug for atorvastatin. It is an inhibitor of the enzyme HMG-CoA reductase, which is involved in cholesterol synthesis and reduces LDL cholesterol levels. Atorvastatin lactone is absorbed from the gut into the bloodstream and then converted to atorvastatin, which has a higher potency than atorvastatin lactone. This conversion occurs in the liver by cytochrome P450 enzymes, including cytochrome CYP3A4. The pharmacokinetics of atorvastatin lactone are influenced by drugs that inhibit these enzymes. Atorvastatin and its metabolites are excreted in human serum as glucuronide or sulfate conjugates.</p>

<p>Travoprost (Fluprostenol isopropyl ester) is used to treat glaucoma and ocular hypertension,is a potent and selective FP prostaglandin receptor agonist.</p>

<p>Orally active atorvastatin inhibits HMG-CoA reductase, lowers lipids, hinders SV-SMC cell growth, and can up thrombotic risk with clopidogrel.</p>

<p>Bexarotene (LGD1069) is a retinoid analogue that is used to treat the skin manifestations of cutaneous T cell lymphoma (CTCL).</p>

<p>Applications Lasofoxifene intermediate.<br>References Rosati, R., et al.: J. Med. Chem., 41, 2928 (1998),<br></p>

<p>Applications 21-Carboxy Dexamethasone is a useful research chemical.<br>References Shepard, Allan R., ACS Chem. Biol., 3, 549-558(2013);<br></p>

<p>Impurity Levonorgestrel EP Impurity G<br>Applications 6α-Hydroxy Levonorgestrel (Levonorgestrel EP Impurity G) is a hydroxylated impurity of Norgestrel (N689500).<br>References Lin, Y., et al.: Biochim. Biophys. Acta, 218, 526 (1970), Smith, K., et al.: J. Steroid Biochem., 32, 445 (1989), Hu, S., et al.: Steroids, 60, 337 (1995),<br></p>

<p>Stability Temperature and Light Sensitive<br>Applications A metabolite of Vitamin D3.<br>References Bell, P.A., et al.: Biochem. J., et al.: 115, 663 (1969), Kumar, R.S., et al.: J. Clin. Invest., 65, 277 (1980), Shimada, K., et al.: Biol. Pharm. Bull., 19, 491 (1996),<br></p>

<p>Applications (3aR,4R,5R,6aS)-4-Formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate is an intermediate in the synthesis of Prostaglandin E2 (P838610), the most common and biologically potent of mammalian prostaglandins.<br>References Radeuchel, B., et al.: Tetrahedron. Lett., 633, 9 (1975);<br></p>

<p>Applications Latanoprost Enol is an impurity of Latanoprost (L177280), a prostaglandin analogue used to treat glaucoma and other degenerative diseases of the eye.<br>References Resul, B., et al.: J. Med. Chem., 36, 2242 (1993);<br></p>

<p>Applications A labelled glucocorticoid microemulsion nasal preparation allergy inhibitor rhinitis.This compound is a mixture of diastereomers at the cyclohexyl acetal.<br>References Fukuoka, E., et al.: Chem. Pharm. Bull., 35, 2943 (1987), Schmitt, E., et al.: J. Pharm. Sci., 88, 291 (1999), Hancock, B., et al.: Pharm. Res., 17, 397 (2000), Hogan, S., et al.: Pharm. Res., 18, 112 (2001).<br></p>

<p>Impurity Calcipotriol EP Impurity C<br>Stability Temperature Sensitive<br>Applications The trans-isomeric impurity of Calcipotriene (C144200) and a vitamin D3 analogue with antitumor effects.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Wietrzyk, J. et al.: Anti-Cancer Drugs, 18, 447 (2007); Wietrzyk, J. et al.: Anticancer Res., 27, 3387 (2007); Filip, B. et al.: J. Ster. Biochem. Mol. Biol., 121, 399 (2010);<br></p>

<p>Applications Estradiols ester used in polymeric matrix for transdermal treatment of osteoporosis.<br>References Tripathi, V.N., et al.: Can. J. Animal Sci., 48, 449 (1968),<br></p>

<p>Applications Exemestane-13C,D3 is the labeled analogue of Exemestane (E957000), an antineoplastic (hormonal).<br>References Giudici, D., et al.: J. Steroid Biochem., 30, 391 (1988), Evans, T.R.J., et al.: Cancer Res., 52, 5933 (1992), Zilembo, N., et al.: Brit. J. Cancer, 72, 1007 (1995)<br></p>

<p>Applications ∆9,11-Dehydro-17α-cyanomethyl estradiol is a metabolite of progestin dienogest (D441870), and is currently being investigated for progesterone-receptor binding, progestational, antiprogestational, estrogenic and antigonadotropic activities for the inhibition of fertility. It is also being considered a novel treatment for heavy menstrual bleeding.<br>References Oettel, M., et al.: Pharmazie, 41, 627 (1993); Kiley, J. &amp; Shulman, L.: Int. J. Womens Health, 3, 281 (2011);<br></p>

<p>Applications An impurity of Atorvastatin.<br>References Graul, A., et al.: Drugs Fut. 22, 956 (1997),<br></p>

<p>Impurity Levonorgestrel EP Impurity C<br>Applications 13-Ethyl-3-ethynyl-18,19-dinor-17α-pregna-3,5-dien-20-yn-17-ol (Levonorgestrel EP Impurity C) is an impurity of Levonorgestrel.<br></p>

<p>Impurity Finasteride EP Impurity B<br>Applications 3-Oxo-4-aza-5α-αndrost-1-ene-17β-carboxylic Acid Methyl Ester (Finasteride EP Impurity B) is an impurity of Finasteride (F342000) and Dutasteride (D735000). An intermediate in the synthesis of Finasteride and Dutasteride, 5α-reductase inhibitors used for treatment of benign prostatic hyperplasia acne, seborrhea, female hirsutism, prostatitis, and prostatic carcinoma and other hyperandrogenetic related disorders. Finasteride impurity.<br>References Bakshi., et al.: J. Med. Chem., 38, 3189 (1995),<br></p>

<p>Applications Estriol 16α,17β-Diacetate is a diacetate derivative of Estriol (E888960); an estrogenic metabolite considerably less potent than the hormone Estradiol (E888000).<br>References Marrian, et al.: Biochem. J., 23,1090 (1929); Huffman, et al.: J. Biol. Chem., 169, 167 (1947)<br></p>

<p>Applications A labelled metabolite of Budesonide (B689490), an antiinflammatory agent.<br>References Cserhati, T., et al.: J. Pharm. Biomed. Anal., 22, 25 (2000), Dilger, K., et al.: J. Clin. Pharmacol., 47, 1532 (2007), Buchwald, P., et al.: Steroids, 73, 193 (2008),<br></p>

<p>Dexamethasone acetate treats rheumatic issues, skin conditions, asthma, allergies, COPD, brain swelling, croup, TB adjunct.</p>

<p>3-(N-Phenyl-N-methyl)aminoacrolein is a hydrophobic compound that has been shown to reversibly bind to serum albumin. This binding leads to a decrease in the lipid content of lipoproteins and a decrease in the rate of their metabolism. These effects are mediated by hydrophobic interactions with the hydrophobic regions of serum albumin. 3-(N-Phenyl-N-methyl)aminoacrolein also interacts with human serum albumin, which is involved in lipid transport and metabolism, and can be used as a contrast agent for X-ray diffraction studies.</p>

<p>Applications Protected Estriol.<br>References Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010),<br></p>

<p>Applications Glucocorticoid.<br></p>

<p>Stability Hygroscopic<br>Applications Prednisolone 21-Sulfate is a metabolite of Prednisolone (P703740).<br>References Hutzler, J., ET AL.: Drug Metab. Dispos., 30, 355 (2002), Sugiyama, D., et al.: J. Biol. Chem., 278, 43489 (2003), Hagenbuch, B., et al.: Xenobiotica, 38, 778 (2008),<br></p>

<p>Applications Testosterone (T155000) derivative.<br></p>

<p>Applications Estriol 3,16α,17β-Triacetate is a triacetate derivative of Estriol (E888960) with contraceptive activity.<br>References Wotiz, H.H., et al.: J. Reprod. Fertil., 26, 363 (1971)<br></p>

<p>Applications N-Des(1,1-dimethylethyl) N-Cyclohexyl Finasteride is an impurity of Finasteride (F342000); an inhibitor of 5α-reductase which is the enzyme that converts testosterone to the more potent androgen 5α-dihydrotestosterone.Also an antialopecia agent.<br>References Koronkowski, M.J., et al.: Pharmacotherapy, 13, 309 (1993); Tenover, J.L., et al.: Clin. Ther., 19, 243 (1997); McConnell, J.D., et al.: N. Engl. J. Med., 338, 557 (1998)<br></p>

<p>Applications Carbenoxolone<br></p>

<p>Applications A Dexamethasone Dipropionate metabolite.<br>References Miyachi, Y., et al.: Steroids, 52, 137 (1988), Soh H., et al.: Brit. J. dermatol., 125, 73 (1991), Civiale, C., et al.: J. Ocul. Pharmacol., Thera., 20, 75 (2004),<br></p>

<p>Applications 21-Butyryloxy Budesonide is a derivative of Budesonide (B689490), a non-halogenated glucocorticoid related to triamcinolone hexacetonide.<br>References Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979); Roth, G., et al.: J. Pharm. Sci., 69, 766 (1980); Clissold, S.P., et al.: Drugs, 28, 485 (1984)<br></p>

<p>Applications 17-Hydroxypregn-5-ene-3,20-dione is used in the synthesis of physiologically active steroid esters and spirolactones that functions as potential aldosterone antagonists.<br>References Seletskii, B. M., et al.: Croat. Chem. Acta. , 58, 699 (1986)<br></p>

<p>Applications A metabolite of Etiocholanolone.<br>References Eriksson, H., et al.: Eur. J. Biochem., 15, 132 (1970), Cook, D., et al.: Endocrinology, 93, 1019 (1973),<br></p>

<p>Applications 17α-Hydroxyprogesterone Heptanoate can be used in therapeutic use and biological study of pharmaceutical compounds and methods of use thereof for treating gender-biased immune disorders.<br>References Stoloff, G., et al.: PCT Int. Appl. WO 2016005599 A1 20160114 (2016)<br></p>

<p>Impurity Levonorgestrel EP Impurity D<br>Applications 13-Ethyl-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (Levonorgestrel EP Impurity D) is an impurity of Levonorgestrel.<br>References McGinty, D., et al.: Endocrinology, 24, 829 (1939), Belanger, A., et al.: Steroids, 37, 361 (1981), Nieman, L., et al.: J. Clin. Endocrinol. Metab., 61, 536 (1985), Klebe, G., et al.: J. Med. Chem., 37, 4130 (1994),<br></p>

<p>Applications 4-Hydroxy Estradiol 1-N3-Adenine is an estrogen metabolite formed with DNA which can lead to the mutations that initiate breast, prostate, and other types of cancer. The N3Ade depurinating adducts could serve as biomarkers to predict the risk of breast cancer.<br>References Chakravarti, D., et al.: Mutat. Res., 456, 17 (2000), Liehr, J., et al.: Endocr. Rev., 21, 4054 (2000), Chakravarti, D., et al.: Oncogene, 20, 7945 (2001), Cavalieri, E., et al.: Chem. Res. Toxicol., 14, 1041 (2002),<br></p>

<p>Applications Epoxy Metradiene is an impurity from synthesis of Fluorometholone (F593145),a glucocorticoid; anti-inflammatory.<br>References Kupferman, A., et al.: Arch. Ophthlmol., 640, 100 (1982); Tokunaga H., et al.: Chem. Pharm. Bull., 32, 4012 (1984);<br></p>

<p>Impurity Progesterone EP Impurity E<br>Applications 20-Dihydroprogesterone Acetate (Progesterone EP Impurity E) is an analogue of Progesterone (P755900), a steroid used in cardiovascular and menopausal studies.<br>References Grodstein, F. et al.: New. Eng. J. Med., 335, 453 (1996); Cushman, M. et al.: Circulation, 100, 717 (1999);<br></p>

<p>Applications Triamcinolone Acetonide (T767165) impurity.<br></p>

<p>(1β,2β)-17-(Acetyloxy)-1,2-dihydro-3'H-cyclopropa[1,2]pregna<br>-1,4,6-triene-3,20-dione; 17-Hydroxy-1 ,2 -methylenepregna<br>-4,6-diene-3,20-dione Acetate; Cyproterone Acetate EP<br>Impurity A<br></p>

<p>Applications 4’-Nitro-3’-(trifluoromethyl)acetanilide is a metabolite of the nonsteroidal antiandrogen drug, Flutamide (F598850).<br>References Kang, P. et al.: Drug Metab. Dispos., 36, 1425 (2008); Takashima, E. et al.: Biol. Pharmac. Bull., 26, 1455 (2003); Katchen, B. et al.: J. Invest. Dermatol., 66, 379 (1976);<br></p>

<p>Impurity Ethinylestradiol EP Impurity M<br>Applications 2-Methylethynylestradiol (Ethinylestradiol EP Impurity M) is a 17α-ethynyl steroid. 2-Methylethynylestradiol is an impurity of Ethynylestradiol (E685100).<br></p>

<p>Applications 25-Hydroxy Cholesterol-d6, is the labeled analogue of 25-Hydroxy Cholesterol (H918030), which is an oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It also induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative regulation of c-Myc.<br>References Aupeix, K. et al.: Immunobiology, 194, 415 (1995); Moog, C. et al.: Antivir. Chem, Chemother., 9, 491 (1998); Ayala-Torres, S. et al.: Exp. Cell Res., 246, 193 (1999);<br></p>

<p>Applications A steroid produced by females having pheromone activities.<br>References Kotiyan, P., et al.: J. Pharm. Biomed. Anal., 22, 667 (2000), Bensafi, M., et al.: Behaviour. Brain Res., 152, 11 (2004), Zhu, B., et al.: Endocrinol., 147, 4132 (2006), Bellavance, E., et al.: J. Med. Chem., 52, 7488 (2009),<br></p>

<p>Applications 4-Methylestrone is an intermediate in the synthesis of 4-substituted estrone and estradiol derivatives with inhibitory activities towards steroid sulfatase as a target for therapeutic intervention of treating breast cancer.<br>References Numazawa, M., et al.: J. Steroid. Biochem. Molec. Biol., 96, 51 (2005);<br></p>

<p>Applications E-17-Deacetylnorgestimate is a metabolite of Norgestimate. A contraceptive for birth control used by women.Note- The oxime isomerizes when: 1) Heated in any solvent or heating the crystalline form 2) Dissolved in MeOH at room temperature very quickly 3) Dissolved in acetone or CHCl3 at room temperature in a couple of hours at room temperature4) In EtOAc or EtOAc/isooctane over a couple of days at RT. It is stable in the crystalline form.<br>References Phillips, A., et al.: Steroids, 55, 373 (1990); Rabiolo, A., et al.: Arch. Gynecol. Obstet., 294, 1317 (2016)<br></p>

<p>Impurity Clobetasol Propionate EP Impurity I<br>Stability Hygroscopic<br>Applications Betamethasone 17-Propionate 21-Mesylate (Clobetasol Propionate EP Impurity I) is the 21-mesylate analogue of Betamethasone 17-Acetate (B327015) with antiinflammatory activity.<br>References Mitsukuchi, M. et al.: Chem. Pharm. Bull., 37, 3286 (1989);<br></p>

<p>Applications Estrone-2,4-d2 (CAS# 350820-16-5) is a useful isotopically labeled research compound.<br></p>

<p>Applications A derivative of Exemestane (E957000), a new aromatase inhibitor.<br>References Thompson, E., et al.: J. Biol. Chem., 249, 5364 (1974), Cole, P., et al.: J. Med. Chem., 33, 2933 (1990), Buzzetti, F., et al.: Steroids, 58, 527 (1993),<br></p>

<p>Stability Hygroscopic<br>Applications A degradation product of Betamethasone (B327000).<br>References Andersson, P., et al.: J. Pharm. Pharmacol., 36, 763 (1984), Wurthwein, G., et al.: Biopharm. Drug Dispos., 11, 381 (1990), Samtani, M., et al.: J. Pharm. Sci., 93, 726 (2004), Samtani, M., et al.: Drug Metab. Dispos., 33, 1124 (2005),<br></p>

<p>Applications Labelled Dutasteride (D735000). Dutasteride is a dual inhibitor of 5α-reductase isoenzymes type 1 and 2; structurally related to Finasteride (F342000). Dutasteride is used in the treatment of benign prostatic hyperplasia.<br>References Bakshi, R.K., et al.: J. Med. Chem., 38, 3189 (1995), Gisleskog, P.O., et al.: Brit. J. Clin. Pharmacol., 47, 53 (1999), Djavan, B., et al.: Expert Opin. Pharmacother., 6, 311 (2005),<br></p>

<p>Applications Obeticholic Acid Methyl Ester is a bile acid derivative useful in research.<br>References Pellicciari, R., et al.: Journal of Medicinal Chemistry, 50, 4265 (2007)<br></p>

<p>Applications (2Z)-2,3-Dehydroxy Atorvastatin is an intermediate in synthesizing (2E)-2,3-Dehydroxy Atorvastatin (D230045), which is an impurity in the synthesis of Atorvastatin (A791750).<br>References Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993); Heinonen, T.M., et al.: Clin. Ther., 18, 853 (1996);<br></p>

<p>Impurity Latanoprost USP Related Compound D<br>Applications Latanoprost derivative. Latanoprost related compound D. Latanoprost USP Related Compound D.<br></p>

<p>Applications Progesterone (P755900) impurity.<br>References Liang, T., et al.: Biol. Chem., 256, 7998 (1981), Bratoeff, E., et al.: J. Steroid Biochem. Mol. Biol., 111, 275 (2008),<br></p>

<p>Applications 6-keto Dexamethasone, is an impurity of Dexamethasone, a glucocorticoid used as an anti-inflammatory agent. Dexamethasone regulates T cell survival, growth, and differentiation. Dexamethasone inhibits the induction of nitric oxide synthase.<br></p>

<p>Applications Betamethasone 21-Acetate-d3, is the labeled analogue of Betamethasone 21-Acetate (B327025), which is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties which can be used in treatment of asthma and itching.<br>References Kerns, E., et al.: J. Pharm. Sci., 90, 1838 (2001), Seidler, J., et al.: J. Med. Chem., 46, 4477 (2003), Alsenz, J., et al.: J. Pharm. Sci., 96, 1748 (2007),<br></p>

<p>Stability Moisture Sensitive<br>Applications (11β,16α)-9-Bromo-21-[(ethoxycarbonyl)oxy]-11-(formyloxy)-17-hydroxy-16-methylpregna-1,4-diene-3,20-dione is an impurity of Dexamethasone (D298800), a glucocorticoid used as an anti-inflammatory agent.<br>References Spangler, M., et al.: Chromatographia, 54(5/6), 329-334 (2001);Wershil, B.K., et al.: Int. Arch. Allergy Immunol., 107, 323 (1995)<br></p>

<p>Stability Temperature Sensitive<br>Applications An epoxy impurity of the selective FP prostaglandin receptor agonist Travoprost (T715600).<br></p>

<p>Applications 3β,5α-Tetrahydrodeoxycorticosterone is a novel derivative of the steroid Dehydroepiandrosterone (DHEA), a known uncompetitive inhibitor of Glucose 6-Phosphate Dehydrogenase (G6PD). Studies have shown that 3β,5α-Tetrahydrodeoxycorticosterone may have potential function in the modulation of calcium and GABAA-gated chloride channel currents found in rat and guinea-pig neurons.<br>References Hamilton, N.M., et al.: J. Medn. Chem., 55, 4431 (2012); Ffench, M., et al.: Steriods., 64, 76 (1999);<br></p>

<p>Applications 6α,9α-Difluoroprednisolone has shown to increase metastases and increase glucocorticoid activity in C57/BL6 mice.<br>References Albert, D., Zeidman, I.: Cancer Res., 22, 1297 (1962)<br></p>

<p>Applications D-Homoanalog of Triamcinolone is a rearrangement product of the drug triamcinolone, an anti-inflammatory drug.<br>References Delaney, E. J.; et al.: Steroids, 59, 196 (1994)<br></p>

<p>Applications A progestogen with low androgenic potency.<br> Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package<br>References Viinikka, L., et al.: Eur. J. Clin. Pharmacol., 15, 349 (1979), Bergink, E.W., et al.: J. Steroid Biochem., 14, 175 (1981)<br></p>