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MedKoo Cat#: 412493 | Name: Cefathiamidine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cefathiamidine is a beta-lactam antibiotic that exhibits a broad spectrum of bactericidal activity against gram-positive bacteria. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis.

Chemical Structure

Cefathiamidine
Cefathiamidine
CAS#33075-00-2

Theoretical Analysis

MedKoo Cat#: 412493

Name: Cefathiamidine

CAS#: 33075-00-2

Chemical Formula: C19H28N4O6S2

Exact Mass: 472.1450

Molecular Weight: 472.58

Elemental Analysis: C, 48.29; H, 5.97; N, 11.86; O, 20.31; S, 13.57

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Cefathiamidine; UNII-8M7CAS5T8L
IUPAC/Chemical Name
(6R,7R)-3-(acetoxymethyl)-7-(2-(((Z)-N,N'-diisopropylcarbamimidoyl)thio)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
JYXACOFERDBGGQ-RHSMWYFYSA-N
InChi Code
InChI=1S/C19H28N4O6S2/c1-9(2)20-19(21-10(3)4)31-8-13(25)22-14-16(26)23-15(18(27)28)12(6-29-11(5)24)7-30-17(14)23/h9-10,14,17H,6-8H2,1-5H3,(H,20,21)(H,22,25)(H,27,28)/t14-,17-/m1/s1
SMILES Code
CC(N/C(SCC(N[C@H]1[C@H]2SCC(COC(C)=O)=C(C(O)=O)N2C1=O)=O)=N/C(C)C)C
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 472.58 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
1: Zhi LJ, Wang L, Chen XK, Zhai XY, Wen L, Dong L, Jacqz-Aigrain E, Shi ZR, Zhao W. Population pharmacokinetics and dosing optimization of cefathiamidine in children with hematologic infection. Drug Des Devel Ther. 2018 Apr 17;12:855-862. doi: 10.2147/DDDT.S160329. PMID: 29713143; PMCID: PMC5909787. 2: Liang J, Yang R, Li X, Bi C, Ye X, Zhang X, Cao W. First four failures of cefathiamidine to treat urogenital gonorrhoea in Guangzhou, China, 2014-15. Sex Health. 2017 Jun;14(3):289-292. doi: 10.1071/SH16087. PMID: 28384434. 3: Zhang XL, Zong MH, Li N. Penicillin acylase-catalyzed synthesis of N-bromoacetyl-7-aminocephalosporanic acid, the key intermediate for the production of cefathiamidine. Bioresour Bioprocess. 2016;3(1):49. doi: 10.1186/s40643-016-0127-3. Epub 2016 Nov 19. PMID: 27917366; PMCID: PMC5116309. 4: Chen HY, Williams JD. The killing effects of cefathiamidine or ampicillin alone and in combination with gentamicin against enterococci. J Antimicrob Chemother. 1983 Jul;12(1):19-26. doi: 10.1093/jac/12.1.19. PMID: 6413484. 5: National pediatric multi-center cooperative group of cefathiamidine observation. [Effects of cefathiamidine on the treatment of children with acute bacterial infectious disease]. Zhonghua Er Ke Za Zhi. 2003 Jan;41(1):54-5. Chinese. PMID: 14761333. 6: Bao Q, Chen L, Wang J. Radiation induced decomposition of a refractory cefathiamidine intermediate. J Environ Sci (China). 2014 Dec 1;26(12):2406-11. doi: 10.1016/j.jes.2014.04.003. Epub 2014 Oct 20. PMID: 25499488. 7: Tze-ying T, Fu W, Chih-lin C, Mei-fang C, Ching-teh C, Ying-yuan C, Yu-kun L. Clinical and laboratory studies of a new cephalosporin derivative-- cefathiamidine. Chin Med J (Engl). 1979 Jan;92(1):26-36. PMID: 105842. 8: Hu M, Hu CQ. [Identification of the degradation compounds of cefathiamidine by liquid chromatography-tandam mass spectrometry]. Yao Xue Xue Bao. 2006 Oct;41(10):1015-9. Chinese. PMID: 17184123. 9: Yang Z, Zhao P, Wang J, Tong L, Cao J, Tian Y, Yao Z, Wang J, Zhu Y, Jia Y, Wen A. DRUGS system enhancing adherence of Chinese surgeons to antibiotic use guidelines during perioperative period. PLoS One. 2014 Aug 22;9(8):e102226. doi: 10.1371/journal.pone.0102226. PMID: 25148306; PMCID: PMC4141742. 10: Fan DF, Yu YC, Ding XS, Nie XL, Wei R, Feng XY, Peng XX, Gao MM, Jia LL, Wang XL. Exploring the drug-induced anemia signals in children using electronic medical records. Expert Opin Drug Saf. 2019 Oct;18(10):993-999. doi: 10.1080/14740338.2019.1645832. Epub 2019 Jul 29. PMID: 31315002.