Basic information
- CAS
56796-20-4- Standard SMILES
CO[C@@]1(NC(=O)CSCC#N)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CS[C@@H]21- InChIKey
SNBUBQHDYVFSQF-HIFRSBDPSA-N- Molecular formula
- C15H17N7O5S3
- Average molar mass
- 471.5 g/mol
- Monoisotopic mass
- 471.04533019
Overview
Cefmetazole is a second-generation cephalosporin antibiotic having N1-methyltetrazol-5-ylthiomethyl, {[(cyanomethyl)sulfanyl]acetyl}amino and methoxy side-groups at positions 3, 7beta and 7alpha respectively of the parent cephem bicyclic structure. It has a role as an antibacterial drug. It is a conjugate acid of a cefmetazole(1-).
Names & identifiers
- Preferred name
- Cefmetazole
- IUPAC
- (6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefmetazole
- Molecular formula
- C15H17N7O5S3
- Molecular weight
- 471.53
Names & synonyms
cefmetazole56796-20-4CefmetazoloCefmetazolum(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidCefmetazol3J962UJT8HCHEBI:3489U-72791DTXSID7022756(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((((cyanomethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-, (6R-cis)-
Show more names
cs1170(6rCMZU 72791U 72791aSKF 83088Cefatrixine
(6R,7S)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-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(6R,7S)-7-((((cyanomethyl)sulfanyl)acetyl)amino)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)sulfanyl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7S)-7-((2-(cyanomethylsulfanyl)acetyl)amino)-7-methoxy-3-((1-methyltetrazol-5-yl)sulfanylmethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid(6R,7S)-7-(2-((cyanomethyl)sulfanyl)acetamido)-7-methoxy-3-(((1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acidRefChem:574974DTXCID502756J01DA40260-384-2
Database identifiers
- CAS
56796-20-4- PubChem CID
- 42008
- DTXSID
DTXSID7022756- ChEMBL
CHEMBL1201195- ChEBI
CHEBI:3489- UNII
- 3J962UJT8H
- EC Number
- 260-384-2
- Nikkaji
- J14.542D
Properties
Computed structural properties
- XLogP
- -0.6
- Topological polar surface area
- 239 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 9
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 818
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP
-2.2
-0.6
Solubility2.16e+00 g/L
Physical DescriptionSolid
Collision Cross Section192.97 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 163 · 163-165C
- Density
- 1.438 · 1.4380 (rough estimate)
- refractive index
- 1.74 · 1.7400 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly, Heated)
- form
- Solid
- pka
- 2.65 · 2.65±0.50(Predicted)
- color
- White
- Water Solubility
- Soluble in water
- InChIKey
- SNBUBQHDYVFSQF-HIFRSBDPSA-N
- SMILES
- N12[C@@]([H])([C@@](NC(CSCC#N)=O)(OC)C1=O)SCC(CSC1N(C)N=NN=1)=C2C(O)=O
- CAS DataBase Reference
- 56796 · 56796-20-4(CAS DataBase Reference)
- FDA UNII
- 3 J962UJT8H · 3J962UJT8H
- ATC code
- 1 DC09 · J01DC09
- Symbol(GHS)
- 7 · GHS07,GHS08
- Signal word
- Warning
- Hazard statements
- 315 · H315-H317-H319-H334-H335
- Precautionary statements
- 261 · P261-P280a-P284-P305+P351+P338-P405-P501a
- Hazard Codes
- Xn
- Risk Statements
- 36 · 36/37/38-42/43
- Safety Statements
- 26 · 26-36
- WGK Germany
- 2 · 2
- RTECS
- 372200 · XI0372200
- HS Code
- 2941906000 · 2941906000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (50%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Cefmetazole
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Safety data
- wgk
- 2
- rtecs
- XI0372200
- hs_code
- 2941906000
- risk_code
- 36/37/38-42/43
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xn
- safety_code
- 26-36
- Hazard statements
- H315-H317-H319-H334-H335
- Precautionary statements
- P261-P280a-P284-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Pharmacodynamics
Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive <i>Proteus</i>, <i>Serratia</i>, anaerobic gram-negative bacilli (including <i>B. fragilis</i>), and some <i>E. coli</i>, <i>Klebsiella</i>, and <i>P. mirabilis</i>, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.
Mechanism of ActionThe bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Biological Half-Life1.50 ±0.14 hours
Metabolism/MetabolitesNo appreciable metabolism.
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and ExcretionBioavailability is approximately 100% following intramuscular injection.
Cellular LocationsExtracellular
Applications
DescriptionCefmetazole is a cephamycin with a nonaromatic side chain at C-7. In addition to a fairly characteristic second-generation cephalosporin antimicrobial spectrum, it possess fairly significant anti-antiaerobic activity. The ejection of its C-3 side chain leads to alcohol intolerance of the disulfuram type and prolonged clotting times.
General DescriptionCefmetazole was synthesized by Sankyo Co. in 1976starting with a biosynthetic cephamycin. It shows excellent activity against Serratia and Proteus, against which cefazolin is not active, and it has stronger activity than cefoxitin, another derivative of cephamycin. Cefmetazole is active against anaerobes and resistant to β-lactamase, but it is not active against Pseudomonas aeruginosa.
UsesSemi-synthetic antibiotic derived from Cephamycin. Antibacterial.
UsesA broad spectrum second generation cephalosporin antibiotic
Suppliers100 total
国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
合肥曼奇诺生物医药技术有限公司19719236623 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
湖北海克斯生化有限公司17362916295; 17362916295 · [email protected]
湖北海克斯生化有限公司18696113233 · [email protected]
Hebei Henghe Import and Export Trading Co. LTD+8618032935937 18032916000 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Sinoway Industrial co., ltd.+86-0592-5800732 +86-13806035118 · [email protected]
江苏普乐司生物科技有限公司0513-66017706 18551496367 · [email protected]
湖北威德利化学试剂有限公司17771473825 13385289472 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]
西安泽邦生物科技有限公司[email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
武汉市皇臻生物化工有限公司13795480948 · [email protected]
NANJING YINGWEN BIOTECHNOLOGY CO LTD+8613382787392 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
天成化工(江苏)有限公司0512-66387919 18662433356 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
潍坊鲁泽新材料有限公司0536-7971999 17176128999 · [email protected]
常州泽源医药科技有限公司19026388314 · [email protected]
常州翔龙医药科技有限公司18915873328 18915873328 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
陕西缔都医药化工有限公司029-81024372 17792795018 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
武汉贝乐叶生物医药科技有限公司18086118078 · [email protected]
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
湖北威德利化学科技有限公司027-83989310 18627915365 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
泰安嘉岳生物化工有限公司15318151873 · [email protected]
武汉沃轩科技有限公司13322067656 · [email protected]
嘉兴市德亿化工有限公司0573-85866609 13325730825 · [email protected]
湖南瑞威尔生物科技有限公司19359985961 · [email protected]
湖北魏氏化学试剂股份有限公司13125137732 18686406941 · [email protected]
广州新长实医药生物科技有限公司19066311943 · [email protected]
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
石家庄瑞田生化有限公司15831127780 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
上海岚克医药科技发展有限公司0086-21-58956006
Additional notes
DefinitionChEBI: A cephalosporin antibiotic containg an N1-methyltetrazol-5-ylthiomethyl side-chain at C-3 of the parent cephem bicyclic structure.
Related reactions
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Compound notes
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