Capreomycin IA

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MedKoo CAT#: 412283

CAS#: 37280-35-6

Description: Capreomycin IA is an antibiotic which is given in combination with other antibiotics for the treatment of tuberculosis. Specifically it is a second line treatment used for active drug resistant tuberculosis. It is given by injection into a vein or muscle.

Chemical Structure

Capreomycin IA
CAS# 37280-35-6

Theoretical Analysis

MedKoo Cat#: 412283
Name: Capreomycin IA
CAS#: 37280-35-6
Chemical Formula: C25H44N14O8
Exact Mass: 668.3467
Molecular Weight: 668.72
Elemental Analysis: C, 44.90; H, 6.63; N, 29.32; O, 19.14

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Capreomycin IA; A250-II; A 250-II; A-250-II

IUPAC/Chemical Name: (S)-3,6-diamino-N-(((2S,5S,11S,15S,Z)-15-amino-2-(hydroxymethyl)-11-((R)-2-iminohexahydropyrimidin-4-yl)-3,6,9,12,16-pentaoxo-8-(ureidomethylene)-1,4,7,10,13-pentaazacyclohexadecan-5-yl)methyl)hexanamide


InChi Code: InChI=1S/C25H44N14O8/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47)/b15-9-/t11-,12-,13+,14-,16-,18-/m0/s1

SMILES Code: NCCC[C@@H](CC(NC[C@@H]1NC([C@@H](NC([C@H](CNC([C@H]([C@H]2CCNC(N2)=N)NC(/C(NC1=O)=C/NC(N)=O)=O)=O)N)=O)CO)=O)=O)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 668.72 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Liu G, Luan B, Liang G, Xing L, Huang L, Wang C, Xu Y. Isolation and identification of four major impurities in capreomycin sulfate. J Chromatogr A. 2018 Oct 12;1571:155-164. doi: 10.1016/j.chroma.2018.08.015. Epub 2018 Aug 7. PMID: 30115387.

2: Thuboy B, Kellermann T, Castel S, Norman J, Joubert A, Garcia-Prats AJ, Hesseling AC, Wiesner L. The determination of capreomycin in human plasma by LC- MS/MS using ion-pairing chromatography and solid-phase extraction. Biomed Chromatogr. 2018 May 3:e4269. doi: 10.1002/bmc.4269. Epub ahead of print. PMID: 29726023.

3: Martin A, Paasch F, Docx S, Fissette K, Imperiale B, Ribón W, González LA, Werngren J, Engström A, Skenders G, Juréen P, Hoffner S, Del Portillo P, Morcillo N, Palomino JC. Multicentre laboratory validation of the colorimetric redox indicator (CRI) assay for the rapid detection of extensively drug- resistant (XDR) Mycobacterium tuberculosis. J Antimicrob Chemother. 2011 Apr;66(4):827-33. doi: 10.1093/jac/dkq527. Epub 2011 Jan 19. PMID: 21393176.

4: Thiara AS, Cundliffe E. Analysis of two capreomycin-resistance determinants from Streptomyces capreolus and characterization of the action of their products. Gene. 1995 Dec 29;167(1-2):121-6. doi: 10.1016/0378-1119(95)00702-4. PMID: 8566762.

5: Nomoto S, Teshima T, Wakamiya T, Shiba T. The revised structure of capreomycin. J Antibiot (Tokyo). 1977 Nov;30(11):955-9. doi: 10.7164/antibiotics.30.955. PMID: 73540.

6: Shiba T, Nomoto S, Wakamiya T. The chemical structure of capreomycin. Experientia. 1976 Sep 15;32(9):1109-11. doi: 10.1007/BF01927571. PMID: 61134.

Additional Information

Common side effects include kidney problems, hearing problems, poor balance, and pain at the site of injection. Other side effects include paralysis resulting in the inability to breathe. It is not recommended with streptomycin or other medications that may damage the auditory vestibular nerve. It is not recommended during pregnancy as it may cause kidney or hearing problems in the baby. Capreomycin is commonly grouped with the aminoglycoside family of medications. How it works is unclear.

Capreomycin was discovered from Streptomyces capreolus in 1960. It was removed from the World Health Organization's List of Essential Medicines in 2019.