Chiral Organic Compounds

Stability Hygroscopic
Applications 10-O-2,2-Dichloroethoxycarbonyl Docetaxel is an impurity of Docetaxel (D494420); an antineoplastic and antimitotic agent that promotes the assembly of micro-tubules and inhibits their de-polymerization to free tubulin.Docetaxel Impurity 1.
References Ringel, I., et al.: J. Natl. Cancer Inst., 83, 288 (1991); Extra, J.-M., et al.: Cancer Res., 53, 1037 (1993)

Impurity Perindopril EP Impurity C
Applications Perindoprilat Lactam A (Perindopril EP Impurity C) is the active metabolite of Perindopril (P287500) in plasma and urine.
References Hillaert, S., et al.: J. Pharm. Biomed. Anal., 25, 775 (2001), Ozoemena, K., et al.: Talanta, 62, 681 (2004),

Applications N-Boc Linagliptin is an impurity of linagliptin (L465900), which is a novel potent and selective dipeptidyl peptidase-4 (DPP-4) inhibitor with potential use in the treatment of type 2 diabetes.
References Prabavathy, N. et al.: Int. J. Pharm. Bio. Sci., 2, 438 (2011); Deacon, C.F.: Diab. Obes. Metab., 13, 7 (2011);

Stability Hygroscopic
Applications 4-Desacetamido-4-chloro Andarine is a Selective Androgen Receptor Modulator (SARM) that has potential use for treatment of androgen related diseases such as muscle wasting and osteoporosis. 4-Desacetamido-4-chloro Andarine also a derivative of Andarine (A637470), a non-steroidal SARM that is used by athletes to enhance performance.
References Jones, A., et al.: Endocrinology, 150, 385 (2009); Marhefka, C., et al.: J. Med. Chem., 47, 993 (2004); Thomas, A., et al.: Rapid Comm. Mass Spec., 24, 1124 (2010)

Applications Biosynthetic precursor of Sphingosine. Inhibits protein kinase C.
References Merrill, A.H. Jr., et al.: Biochemistry, 28, 3138 (1989)

Impurity Rac-Vildagliptin Impurity F
Applications Vildagliptin Lactam is an impurity of Vildagliptin (V305000). Glyptins are class of oral anti-hyperglycemic agents that inhibit dipeptidyl peptidase 4 (DPP-4), which can act as a serine exopeptidase. ASide from there use in type 2 diabetes, gliptins have positive cardiovascular and anti-inflammtatory effects. Antidiabetic.
References Ahren, B., et al.: J. Clin. Endocrinol. Metab., 89, 2078 (2004), Ahren, B., et al.: Diabetes Care, 27, 2874 (2004), Barlocco, D., et al.: Curr. Opin. Invest. Drugs, 5, 1094 (2004),

Impurity Orlistat USP Related Compound D
Applications N-Formyl-L-leucine (3S,4R,6S)-3-Hexyltetrahydro-2-oxo-6-undecyl-2H-pyran-4-yl ester is an impurity of Orlistat (O686500). Orlistat USP Related Compound D.
References Stalder, H., et al.: Helv. Chim. Acta , 75, 1593 (1992),

Applications Rivaroxaban Pseudodimer is an impurity of Rivaroxaban (R538000), a novel antithrombotic agent. A highly potent and selective, direct FXa inhibitor.
References Ansell, J., et al.: Drugs, 64, 1 (2004), Eriksson, B., et al.: J. Thromb. Haemost., 3, 103 (2005), Kubitza, D., et al.: Clin. Pharmacol. Ther., 78, 412 (2005),

Impurity Pramipexole Related Compound G
Applications Pramipexole derivative used for the preparation of (S)-Pramipexole via resolution of 2,6-diamino-7-hydroxy-4,5,6,7-tetrahydrobenzothiazole derivatives.
References Validation of a column liquid chromatographic method for the analysis of pramipexole and its 5 impurities. Journal of AOAC International (2010), 93(4), 1102-1112. Gegoe, Csaba Lehel; Fejes, Imre; Garaczi, Sandor; Kovacs, Imre; Lukacs, Ferenc; Majercsik, Orsolya; Schneider, Geza. Process for preparation of (S)-pramipexole via resolution of 2,6-diamino-7-hydroxy-4,5,6,7-tetrahydrobenzothiazole derivatives. Eur. Pat. Appl. (2008), 26pp. CODEN: EPXXDW EP 1878731

Impurity Perindopril EP Impurity F
Applications Perindopril Diketopiperazine (Perindopril EP Impurity F) is an impurity of Perindopril (P287500).
References Koenigbauer, M., et al.: Pharm. Res., 11, 777 (1994), Andres, C., et al.: Int. J. Pharm., 218, 153 (2001), Chadha, R., et al.: Pharmazie, 58, 631 (2003),

Applications Repaglinide impurity.
References Grell, W., et al.: J. Med. Chem., 41, 5219 (1998),

Applications (S)-β-Isopropylphenethylamine is an intermediate in the process for producing optically active Flurbiprofen (F598700).
References Magnus, M., et al.: Nature, 38, 3491 (1997), Agranat, I., et al.: Nat. Rev. Drug Discovery., 1, 753 (2002),

Applications 4H-Furo[3,2-c]pyranyl Mupirocin Methyl Ester is an intermediate in the synthesis of 4H-Furo[2,3-c]pyranyl Mupirocin Sodium Impurity (F864850), which is also a mupirocin (M794000) impurity. The rearrangement isomer of Mupirocin is prepared using an enzyme-catalyzed, selective deesterification.
References Sime, J.T., et al.: Tetrahedron Lett., 28, 5169 (1987),

Applications (1RS)-1-(3,5-Dihydroxyphenyl)2-[[(1RS)-2-(4-hydroxy-3-methylphenyl)-1-methylethyl]aminoethanol Hydrobromide is an impurity of Fenoterol Hydrobromide (F248850); a β2-adrenergic agonist. Also a bronchodilator and tocolytic.
References Schuster, B., et al. Arzneim.-Forsch., 19, 1905 (1969); Gerris, J., et al.: Eur. J. Clin. Pharmacol., 18, 443 (1980); Heel, R.C., et al.: Drugs, 15, 3 (1978)

Stability Hygroscopic
Applications Docetaxel (D494420) injection impurity A.
References Vasu Dev, R., et al.: J. Pharm. Biomed. Anal., 40, 614 (2006),

Impurity Timolol EP A; Timolol BP Impurity A; Timolol USP Related Compound A
Applications Antihypertensive; antiarrhythmic (class II); antianginal; antiglaucoma agent.Timolol EP A; Timolol BP Impurity A; Timolol USP Related Compound A
References Wasson, et al.: J. Med. Chem., 15, 651 (1972), Franciosa, et al.: Clin. Pharmacol. Ther., 13, 138 (1972), Heel, R.C., et al.: Drugs, 17, 38 (1979), Rofman, B.A., et al.: Hypertension, 2, 643 (1980), Mazzo, D.J., et al.: Anal. Profiles Drug Subs., 16, 641 (1987),

Applications Mitomycin (M371900) impurity.
References Siegel, D., et al.: Biochemistry, 31, 7879 (1992), Kontou, M., et al.: Oncogene, 21, 2406 (2002),

Impurity Docetaxel EP Impurity D
Applications 7-Epi-10-oxo Docetaxel (Docetaxel EP Impurity D) is a Docetaxel (D494420) injection impurity D.
References Hanna, I., et al.: Cancer Res., 60, 3440 (2000), Bournique, B., et al.: Br. J. Clin. Pharmacol., 52, 53 (2001), McFadyen, M., et al.: Biochem. Pharmacol., 62, 207 (2001), Vasu Dev, R., et al.: J. Pharm. Biomed. Anal., 40, 614 (2006),

Applications Desacetyl Forskolin is an analogue of Forskolin (F701800). Desacetyl Forskolin was tested for its ability to activate rat brain adenylate cyclase, activate detergent-solubilized rat brain adenylate cyclase, increase cyclic AMP in intact S49 wild-type cells, and inhibit the binding of 3H-forskolin to rat brain membranes.
References Desouza, N., et al.: Med. Res. Rev., 3, 201 (1983); Seamon, K., et al.: J. Med. Chem., 26, 436 (1983); Seguin, E., et al.: Planta Medica, 54, 4 (1988);

Applications N-Jasmonyl-L-Isoleucine (Mixture of Diastereomers) is a plant horomone.
References Chen, Y., Chen, Z.: J. Separation Sci., 36, 892 (2013)

Applications Bisabolene is a sesquiterpene and can be extracted from oregano and other aromatic plants. It may be a potential anticancer agent that can induce apoptosis in A549 cancer cell line.
References Grosso, N. R., et al.: Argent., Pat. Appl. AR 90961 A1 20141217 (2014); Yfanti, P., et al.: Am J Plant Sci. 6, 2092 (2015)

Stability Hygroscopic
Applications Deoxypyridinoline Chloride Trihydrochloride Salt a collagen cross-links agent. A primary reference material for the monitoring of bone metabolism.
References Heaney, R., et al.: J. Bone Miner. Res., 5, 1135 (1990), Hannon, R., et al.: J. Bone Miner. Res., 13, 1124 (1998), Coudray, C., et al.: Eur. J. Nutr., 42, 91 (2003), Abrams, S., et al.: Am. J. Clin. Nutr., 82, 471 (2005),

Applications A new calcium sensing receptor ligand demonstrating potent calcilytic activity.
References Ray, N., et al.: J. Bone Miner. Res., 12, 24 (1997), Sato, M., et al.: J. Med. Chem., 42, 1 (1999),Rodan, G., et al.: Science, 289, 1508 (2000), Goltzman, D., et al.: Nat. Rev. Drug Discov., 1, 784 (2002), Petrel, C., et al.: J. Biol. Chem., 279, 18990 (2004),

Applications A potent novel activators of large-conductance Ca2+-activated K+ channel.
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 Imaizumei, Y. et al.: Mol. Pharmacol., 62, 836 (2002); Chang, S. et al.: AM. J. Physiol., 298, F1416 (2010);

Applications GDC 0152 is a peptidomimetic small molecule antagonist of inhibitor of apoptosis (IAP) proteins with antitumor activity.
References Yue, Q., et. al.: Drug Metab. Dispos., 41, 508 (2013)

Stability Very Hygroscopic
Applications 2-O-α-D-Glucosylglycerol is used to prepare glycoglycerolipid analogs active as antitumor-promoters the influence of the anomeric configuration.
References Colombo, D., et al.: Eur. J. Med. Chem., 35, 1109 (2000);

Impurity Tadalafil EP Impurity B
Applications Tadalafil (T004500) analog. Tadalafil Impurity (6S,12aS)
References Daugan, A., et al.: J. Med. Chem., 46, 4533 (2003), Jiang, W., et al.: Bioorg. Med. Chem., 12, 1505 (2004),

Impurity Tadalafil EP Impurity C
Applications The (6S)-cis-enantiomer of Tadalafil (T004500). Tadalafil Impurity (6S,12aR)
References Aldridge, J., et al.: Br. Med. J., 318, 669 (1999), Daugan, A., et al.: J. Med. Chem., 46, 4533 (2003), Vredenbregt, M., et al.: J. Pharm. Biomed. Anal., 40, 840 (2006),

Impurity Tadalafil EP Impurity A
Applications The (6R)-cis-enantiomer of Tadalafil (T004500). Tadalafil Impurity (6R,12aS)
References Aldridge, J., et al.: Br. Med. J., 318, 669 (1999), Daugan, A., et al.: J. Med. Chem., 46, 4533 (2003), Vredenbregt, M., et al.: J. Pharm. Biomed. Anal., 40, 840 (2006),

Stability Hygroscopic
Applications (±)-17-Methyl-morphinan-3-ol Hydrobromide is a racemic mixture of Dextrorphan Tartrate Salt (D299485) and Levorphanol Tartrate (L376500). Dextrorphan Tartrate Salt and Levorphanol Tartrate are orally active synthetic morphine analogs and analgesics (narcotic). Levorphanol Tartrate is a controlled substance.
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 Tallarida, R., et al.: Life Sci., 45, 947 (1989); Netzer, R., et al.: Eur. J. Pharmacol., 238, 209 (1993); Mao, J., et al.: Pain, 67, 361 (1996); Chow, L., et al.: J. Biomed. Sci., 11, 717 (2004); Randall, L.O., et al.: J. Pharmacol. Exp. Ther., 99, 163 (1950); Dajani, E., et al.: Eur. J. Pharmacol., 34, 105 (1975); Winpenny, J., et al.: Drugs, 8, 416 (2005),

Applications N-[3-(N-L-Alanyl)-amino-3-carboxypropyl]-D-histidine is an analog of Nicotianamine (N408500), a phytosiderophore that is produced in higher plants as iron chelating amino acids that promote uptake of iron from soil. Nicotianamine (N408500) biosynthesis in plants depicts the association of three enzymatic activities: a histidine racemase, an enzyme distantly related to nicotianamine synthase, and a staphylopine dehydrogenase belonging to the DUF2338 family.
References Klair, S., et al.: J. Plant Nutr., 19, 1295 (1996); Ghssein, G.; et al.: Science, 352, 1105 (2016)

Stability: Hygroscopic
Applications: (1R,2S)-Norephedrine Hydrochloride is a hydrochloride salt of (1R,2S)-Norephedrine (N674400), a metabolite of Phenmetrazine, an ephedrine alkaloid and a nervous system stimulant.
References Jian, Z., et al.: Planta Med., 54, 69 (1988);Tanaka, T., et al.: Nat. Med., 49, 418 (1995);Marchei, E., et al.: J. Pharm. Biomed. Anal., 41, 1633 (2006)

Applications Intermediate in the preparation of Ertapenem (E635000).

Applications: D-(-)-Pseudoephedrine, is an enantiomer of (+)-Pseudoephedrine Hydrochloride (P839350), a non-selective adrenergic agonist, used as nasal decongestant.Controlled precursor.
References Fairchild, M.D., et al.: J. Pharmacol. Exp. Ther., 158, 135 (1967); Hughes, D.T.D., et al.: J. Clin. Hosp. Pharm., 8, 315 (1983); Gurley, B.J., et al.: J. Pharm. Sci., 87, 1547 (1998);

Stability Hygroscopic
Applications A metabolite of Pravastatin, a competitive inhibitor of HMG-CoA reductase. Bioactive metabolite of mevastatin.
References Serizawa, N., et al.: J. Antibiot., 36, 604 (1983), White, H.D, et al.: N. Engl. J. Med., 343, 317 (2000),