Steroids and Derivatives

Applications 3-Aminobenzotrifluoride is a known human toxin that can cause bacterial mutation and hepatocyte unscheduled DNA synthesis.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Reinhold, D., et al.: T. ASAE, 49, 2077 (2006); Thompson, C., et al.: Environ. Mutagen., 5, 803 (1983)

Stability Hygroscopic
Applications Cardiotonic.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Foerster, et al.: Arch. Int. Pharmacodyn. Ther., 159, 1 (1966), Jakovljevic, I.M., Anal. Profiles Drug Subs., 3, 149 (1974)

Applications 23-Hydroxybudesonide is an metabolite of budesonide (B689490), a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.
References Edsbaecker, S., et al.: Drug. Metabol. Dispostion., 15, 403 (1987); Moore, C.D., et al.: Drug. Metabolism. Disposition., 41, 379 (2013);

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

Applications A potential metabolite of Exemestane (E957000).
References Buzzetti, F., et al.: Steroids, 58, 527 (1993),

Applications Protected Estradiol. Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.
References Miilunpohja, M., et al.: J. Steroid Biochem. Mol. Biol., 100, 59 (2006), Ikonomou, M., et al.: Environ. Toxicol. Chem., 27, 243 (2008),

Stability Hygroscopic
Applications 6-Bromo-Betamethasone 17,21-Dipropionate (Betamethasone Dipropionate EP Impurity H) is an impurity of Betamethasone (B327000), a glucocorticoid used as an anti-inflammatory agent.
References Ferrante, M.G., et al.: Anal. Profiles Drug Subs., 6, 43 (1977); Li, A., et al.: Chem. Biol. Interact., 142, 7 (2002); Cruz-Monteagudo, M., et al.: Eur. J. Med. Chem., 40, 1030 (2005)

Applications 17α-Hydroxy-progesterone Valerate acts as a synthetic Progesterone (P755900) reducing the chance of pre-term birth in women. Progesterone is a steroid hormone produced by the corpus luteum. Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation
References Anderson, E., et al.: Breast Cancer Res., 4, 197 (2002), Lanari, C., et al.: Breast Cancer Res., 4, 240 (2002), Albrecht, E.D., et al.: Front. Biosci., 8, 416 (2003), Qiu, M., et al.: J. Steroid Biochem. Mol. Biol., 85, 147 (2003),

Applications 2,5-Bis(trifluoromethyl)aniline is a haloalkul substituted aniline used in the preparation of anti-benign prostatic hyperplasia drug, Dutasteride (D735000).
References Liang, Y. et al.: Jil. Dax. Xueb. Lixeub., 45, 1035 (2007);

Applications E-Ospemifene is the E-isomer of Ospemifene (O703000) and is useful for lowering serum cholesterol. It acts as a antiatherosclerotic and is also estrogen-like.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Sodervall, M., et al.: PCT Int. Appl. WO 9942427 A1 19990826. Aug 26, 1999

Applications Dexamethasone-biotin is biotin labelled Dexamethasone. Dexamethasone is a glucocorticoid used as an anti-inflammatory agent. Dexamethasone regulates T cell survival, growth, and differentiation. Dexamethasone inhibits the induction of nitric oxide synthase.
References Wershil, B.K., et al.: Int. Arch. Allergy Immunol., 107, 323 (1995), Riccardi, C., et al.: Cell Death Diff., 6, 1182 (1999), Llanos, S.L. and Roldan, A.: Bio Cell, 23, 29 (1999)

Impurity Atorvastatin 2-Hydroxy Lactone
Stability Hygroscopic
Applications A metabolite of Atorvastatin, a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.

Applications Testosterone Isocaproate, is one of the common anabolic steroid esters. It is a controlled substance in US due to their potential for abuse and misuse. It can be used for the treatment of constitutional delayed puberty (CDP), in combination of other testosterone esters.
References Noggie, F. T., et al.: J. Chromatography. Sci., 28 (5), 263 (1990); Buyukgebiz, A., et al.: Hormone REs., 44 Suppl 3, 32 (1995);

Applications A labelled metabolite of Equilin (E592800).
References Enmark, E., et al.: J. Clin. Endocrinol. Metab., 82, 4258 (1997), Wang, Z., et al.: J. Med. Chem., 43, 2419 (2000), Jiang, X., et al.: Steroids, 71, 334 (2006),

Impurity Fulvestrant Impurity E;
Applications Fulvestrant (F862500) impurity E.

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

Applications 17α,21-Dideoxy-6α,​9α-Difluoroprednisolone is an impurity of the drug Difluprednate (D445925). Difluprednate is a corticosteroid (derivative of prednisolone), approved for the treatment of post-operative ocular inflammation.
References Kapp, A., et al.: J. Allergy and Clin. Immunol., 110, 277 (2002); Yasueda, S., et al.: J. Pharm. Biomed. Anal., 30, 1735 (2003); Yamaguchi, M., et al.: Int. J. Pharm., 301, 121 (2005)

Applications Atorvastatin-d5 tert-Butyl Ester is the labeled analogue of Atorvastatin tert-Butyl Ester (A791740), an impurity arising in the synthesis of Atorvastatin (A791750), a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia.
References Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993); Heinonen, T.M., et al.: Clin. Ther., 18, 853 (1996); Whitfield, L.R., et al.: Eur. J. Drug Metab. Pharmacokinet., 25, 97 (2000)

Applications 2-Hydroxy-estrone-6-N3-adenine is a depurinating adduct that is created by the interaction of specific metabolites of estrogens in the body with DNA. Unfortunately, these adducts are endogenous initiators of various human cancers, such as breast & prostate.
References Yang, L., et al.: Prostate, 69, 41 (2009); Zahid, M., et al.: Chem. Res. Toxicol., 19, 164 (2006); Zhang, Y., et al.: Metabol. Clin. Exp., 56, 887 (2007)

Applications Labelled Cortisol-d4 21-Sulfate (C696320). Cortisol 21-Sulfate is a phase II metabolite of Cortisol (H714615).
References Spielgelhalder, B., et al.: J. Steroid Biochem., 7, 749 (1976), Vanluchene, E., et al.: J. Chromatogr., 456, 175 (1988), Choi, M., et al.: Steroids, 65, 54 (2000),

Applications Labelled Bexarotene (B336750). Used as an antineoplastic. A selective retinoid X receptor (RXR) agonist.
References Boehm, M.F., et al.: J. Med. Che., 37,2930 (1994), Gottardis, M.M., et al.: Cancer Res., 56, 5566 (1996), Mukherjee, R., et al.: Nature, 386, 407 (1997), Miller, V.A., et al.: J. Clin. Oncol., 15, 790 (1997)

Stability Light Sensitive, Temperature Sensitive
Applications An Atorvastatin (A791750) derivative which have improved stability.

Applications Labelled Testosterone (T155000). Principal hormone of the testes, produced by the interstitial cells. Major circulating androgen; converted by 5α-reductase in androgen-dependent target tissues to 5α-dehydrotestosterone which is required for normal male sexual differentiation. Also converted by aromatization to Estradiol.Controlled substance (anabolic steroid). Androgen.
References McFarland, K., et al.: Science, 245, 494 (1989), Heckert, L., et al.: Mol. Endocrinol., 12, 1499 (1998), Themmen, A., et al.: Endocr. Rev. 21, 551 (2000), Kumar, R., et al.: Biol. Reprod., 65, 710 (2001),

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.
References Numazawa, M., et al.: J. Steroid. Biochem. Molec. Biol., 96, 51 (2005);

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).
References Kearney, A.S., et al.: Pharm. Res., 10, 1461 (1993); Heinonen, T.M., et al.: Clin. Ther., 18, 853 (1996);

Applications Glucocorticoid.

Impurity Dutasteride EP Impurity F
Applications 1-Chloro Dihydro Dutasteride (Dutateride EP Impurity F) is a 3-oxo-4-aza-5α-androstene-17β-carboxylic acid derivative and an impurity of Dutasteride (D735000).

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.
References Stoloff, G., et al.: PCT Int. Appl. WO 2016005599 A1 20160114 (2016)

Impurity Levonorgestrel EP Impurity D
Applications 13-Ethyl-18,19-dinor-17α-pregn-4-en-20-yn-17-ol (Levonorgestrel EP Impurity D) is an impurity of Levonorgestrel.
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),

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.
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),

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

Applications Testosterone-16,16,17-d3 17-Phenylpropionate, is the labeled analogue of Testosterone 17-Phenylpropionate (T155150), a Testosterone ester being misused by athletes in an attempt to improve sports performance. It can also be used as a therapy in glucocorticoid-treated patients to increase the circulating testosterone concentration.
References Shackleton, C. H. L., et al.: Steroids, 62 (7), 523 (1997); Reid, I. R., et al.: Archives Internal Med., 156 (11), 1173 (1996);

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.
References Phillips, A., et al.: Steroids, 55, 373 (1990); Rabiolo, A., et al.: Arch. Gynecol. Obstet., 294, 1317 (2016)

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

Applications Anti-inflammatory (topical).
References Kirshbaum, J., et al.: Anal. Profiles Drug Subs., 8, 251 (1979),

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.

Stability Temperature Sensitive
Applications An epoxy impurity of the selective FP prostaglandin receptor agonist Travoprost (T715600).

Impurity Latanoprost USP Related Compound B
Applications An impurity of commercially prepared Latanoprost (L177280). Latanoprost USP Related Compound B.
References Resul, B., et al.: J. Med. Chem., 36, 2242 (1993),

Applications The minor metabolite of Deflazacort.
References Bernareggi, A., et al.: J. Pharma. Biomed. Anal., 5, 177-81 (1987), Assandri, A., et al.: Xenobiotica, 13(3), 185 (1983), Martinelli, E., et al.: Drug Metab. Dispos., 7, 335 (1979),

Applications 16α-Hydroxypregna-4,9(11)-diene-3,20-dione is an intermediate in the synthesis of 16-Hydroxycorticosterone 20-Hydroxy-21-Acid (H918430), an oxidized derivative of corticosterone (C695700).
References Allen, G.R., et al.: J. Am. Chem. Soc., 81, 4968 (1959);

Applications 21-Butyryloxy Budesonide is a derivative of Budesonide (B689490), a non-halogenated glucocorticoid related to triamcinolone hexacetonide.
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)

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.
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),

Applications Estrone Enol Diacetate can be applied as a substrate for human paroxonases. A steroid with potential to be inhibitor of NADH-oxidase and succinate oxidase.
References Teiber, J. et al.: Arch. Biochem. Bioiphys. 461, 24 (2007); Stoppani, A. et al.: Arch. Biochem. Biophys., 127, 463 (1968)

Stability Not stable in Acidic or basic condition
Applications 6β-Methyl Fluorometholone is an impurity in the synthesis of Fluorometholone (F593145), a glucocorticoid; anti-inflammatory.
References Kupferman, A., et al.: Arch. Ophthlmol., 640, 100 (1982), Tokunaga H., et al.: Chem. Pharm. Bull., 32, 4012 (1984),

Applications A derivative of Exemestane (E957000), a new aromatase inhibitor.
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),

Applications Carbenoxolone

Applications (11β)-9-Fluoro-11,21-dihydroxy-16-methyl-pregna-1,4,16-triene-3,20-dione is a derivative of Dexamethasone (D298800), an anti-inflammatory glucocorticoid.
References Kodelja, V., et al.: J. Immunol., 160, 1411 (1998), Metselaar, J., et al.: Arthritis Rheum., 48, 2059 (2003), Buttgereit, F., et al.: Arthritis Rheum., 50, 3408 (2004), Martinez, F., et al.: Front Biosci., 13, 453 (2008),

Applications (20S)-21-Hydroxy-20-methylpregn-4-en-3-one is a side chain degradation product of natural sterols. It is also an intermediate in the preparation of follicular fluid-meiosis activating sterol.
References Andor, A. et al.: Appl. Environ. Microbiol., 72, 6554 (2006); Blume, T. et al.: Org, Lett., 5, 1837 (2003);

Applications 6β-Hydroxy Betamethasone can be used as analyte in analytical study for detecting betamethasone metabolites in human urine using liquid chromatography coupled to tandem mass spectrometry.
References Matabosch, X., et al.: Drug Testing and Analysis, 7, 663-672 (2015)

Applications 4’-Nitro-3’-(trifluoromethyl)acetanilide is a metabolite of the nonsteroidal antiandrogen drug, Flutamide (F598850).
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);

Applications 20α-Dihydro Pregnenolone is a metabolite of Pregnenolone (P712200).
References Purdy, R., et al.: J. Med. Chem., 33, 1572 (1990), Bixo, M., et al.: Brain Res., 764, 173 (1997), Huang, X., et al.: J. Biol. Chem., 275, 29452 (2000),

Impurity Levonorgestrel EP Impurity B
Applications 13-Ethyl-17-hydroxy-18,19-dinor-17α-pregn-5(10)-en-20-yn-3-one (Levonorgestrel EP Impurity B) is an impurity of Levonorgestrel.
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),

Applications A labelled metabolite of Exemestane; exerts biological effects as an androgen.
References Howell, A., et al.: Lancet, 365, 60 (2005), Goss, P., et al.: Clin. Cancer Res., 10, 5717 (2004), Buzdar, A., et al.: Lancet Oncol., 7, 633 (2006), Coates, A., et al.: J. Clin. Oncol., 25, 486 (2007), Jordan, V., et al.: Steroids, 72, 7 (2007),

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.
References Seletskii, B. M., et al.: Croat. Chem. Acta. , 58, 699 (1986)

Applications Finasteride Carboxylic Acid Methyl Ester is an metabolite of Finasteride (F342000), an inhibitor of 5α-reductase, the enzyme which converts testosterone to the more potent androgen, 5α-dihydrotestosterone.
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),

Applications 1,2-Dihydro Triamcinolone is a derivative of Triamcinolone (T767165), a glucocorticoid, antiasthmatic (inhalant); antiallergic (nasal).
References Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972); Bernstein, I.L., et al.: Chest, 81, 20 (1982);

Impurity Budesonide EP Impurity J
Applications 9α-Bromobudesonide (Budesonide EP Impurity J) is an impurity of Budesonide (B689460), a non-halogenated glucocorticoid intended for the local treatment of lung disease.
References Ryrfeldt, Å., et al.: Eur. J. Respir. Dis., 122, 86 (1981); Vestbo, J., et al.: Lancet, 353, 1819 (1999)

Applications A metabolite of the neuroactive steroid Progesterone (PROG) (P755900).
References Wiebe, J., et al.: Cancer Res., 60, 936 (2000), Lacasa, D., et al.: J. Biol. Chem., 276, 11512 (2001), Johansson, I., et al.: Brain Res., 934, 125 (2002), Leonhardt, S., et al.: Steroids, 68, 761 (2003),

Applications Testosterone (T155000) derivative.

Applications 5,6-Dehydro-17α-dutasteride is an epimer of 5,6-Dehydro-17β-dutasteride (D229560) an impurity in the synthesis of Dutasteride (D735000), 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.
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),

Applications 6α-Spiro[androsta-1,4-diene-6,2'-oxiran]-3,17-dione is a metabolite of exemestane (E957000). Exemestane is an antineoplastic (hormonal).
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)

Applications Ulipristal is a selective progesterone receptor modulator. Ulipristal is used as an emergency contraceptive.
References Gronemeijer, H., et al.: J. Steroid Biochem., 40, 271 (1991), Spitz, I., et al.: Contraception, 48, 403 (1993), Conneely, O., et al.: Steroids, 68, 771 (2003), Chwalisz, K., et al.: Endocr. Rev., 26, 423 (2005),

Applications (5α)-Pregnane-3,20-dione exerts neuroprotective effects in chronic autoimmune encephalomyelitis (EAE). The neuroactivity of the steroid acts as a therapeutic agent for multiple sclerosis.
References Caruso, D. et al.: J. Neuroendocrinol., 24, 851 (2012);

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

Applications Labelled Budesonide, a non-halogenated glucocorticoid related to triamcinolone hexacetonide. Used as an antiinflammatory agent.
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),

Applications α,α,α-Trifluorotoluene, is used as a specialty solvent in organic synthesis and an intermediate in the production of pesticides and pharmaceuticals.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Skelly, P. D., et al.: Handbook for Critical Cleaning, 1, 191 (2011);

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

(betaR,deltaR)-2,3-Bis(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid hemicalcium salt is an impurity that is used in the production of a drug product. This product is metabolized to (betaR,deltaR)-2,3-bis(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-4-[(phenylamino)carbonyl]-1H-pyrrole 1 heptanoic acid which is used as an analytical standard for HPLC.