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66309-69-1 molecular structure
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(6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

ChemBase ID: 114
Molecular Formular: C18H23N9O4S3
Molecular Mass: 525.62812
Monoisotopic Mass: 525.10351326
SMILES and InChIs

SMILES:
S1[C@H]2N(C(=O)[C@H]2NC(=O)Cc2nc(sc2)N)C(=C(C1)CSc1n(nnn1)CCN(C)C)C(=O)O
Canonical SMILES:
CN(CCn1nnnc1SCC1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)Cc1csc(n1)N)C
InChI:
InChI=1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1
InChIKey:
QYQDKDWGWDOFFU-IUODEOHRSA-N

Cite this record

CBID:114 http://www.chembase.cn/molecule-114.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(6R,7R)-7-[2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-[({1-[2-(dimethylamino)ethyl]-1H-1,2,3,4-tetrazol-5-yl}sulfanyl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IUPAC Traditional name
cefotiam
Brand Name
Ceradon
Synonyms
Cefotiam hydrochloride
Cefotiamum [INN-Latin]
CTM
Cefotiam
Abbott 48999
Spizef
Sporidyn
Cefotiam Dihydrochloride
(6R,7R)-7-[[2-(2-Amino-4-thiazolyl)acetyl]amino]-3-[[[1-[2-(dimethylamino)ethyl]-1H-tetrazol-5-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Hydrochloride
CAS Number
66309-69-1
61622-34-2
PubChem SID
46506679
160963577
PubChem CID
43708

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
C243005 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 2.794902  H Acceptors 10 
H Donor LogD (pH = 5.5) -3.1281393 
LogD (pH = 7.4) -3.1065228  Log P -3.0857437 
Molar Refractivity 142.3365 cm3 Polarizability 48.78519 Å3
Polar Surface Area 172.46 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five false 
Log P -0.33  LOG S -2.61 
Solubility (Water) 1.29e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Soluble expand Show data source
Hydrophobicity(logP)
-2.1 expand Show data source
Storage Condition
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

TRC TRC DrugBank DrugBank
Toronto Research Chemicals - C243005 external link
Cephalosporin Antibiotic.
DrugBank - DB00229 external link
Item Information
Drug Groups approved
Description One of the cephalosporins that has a broad spectrum of activity against both gram-positive and gram-negative microorganisms. [PubChem]
Indication For treatment of severe infections caused by susceptible bacteria.
Pharmacology Cefotiam is a third generation beta-lactam cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. Cefotiam works by inhibiting bacterial cell wall biosynthesis.
Toxicity Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected Organisms
Enteric bacteria and other eubacteria
Absorption Rapidly absorbed following intramuscular injection. Bioavailability is 60% following intramuscular injection.
Half Life Approximately 1 hour.
Protein Binding 40%
References
Muller R, Bottger C, Wichmann G: Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. Arzneimittelforschung. 2003;53(2):126-32. [Pubmed]
Kolben M, Mandoki E, Ulm K, Freitag K: Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. Eur J Clin Microbiol Infect Dis. 2001 Jan;20(1):40-2. [Pubmed]
Shimizu S, Chen KR, Miyakawa S: Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. Dermatology. 1996;192(2):174-6. [Pubmed]
External Links
Wikipedia

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Muller R, Bottger C, Wichmann G: Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. Arzneimittelforschung. 2003;53(2):126-32. Pubmed
  • • Kolben M, Mandoki E, Ulm K, Freitag K: Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. Eur J Clin Microbiol Infect Dis. 2001 Jan;20(1):40-2. Pubmed
  • • Shimizu S, Chen KR, Miyakawa S: Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. Dermatology. 1996;192(2):174-6. Pubmed
  • • Murata, H., et al.: J. Hepatol., 38, 573 (2003)
  • • Osawa, M., et al.: Legal Med., 10, 143 (2003)
  • • Fliri, A., et al.: J. Med. Chem., 52, 8038 (2003)
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PATENTS

PATENTS

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INTERNET

INTERNET

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