Cefazolin

Athanor · official

C₁₄H₁₄N₈O₄S₃ · 454.5 g/mol

IUPAC name: 3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Also called Ancef, Kefzol, first generation

Drugs

Open in Athanor

Drawn from its SMILES with RDKit

Names and identifiers

IUPAC name: 3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Synonyms: Ancef, Kefzol, first generation
+ 36 more
DTXSID10860354, 3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-((2-(1H-tetrazol-1-yl)acetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[2-(1H-tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, RefChem:1066252, DTXCID90208750, 3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, Cephamezine;Cephazoline, 3-[(5-methyl(1,3,4-thiadiazol-2-ylthio))methyl]-6-oxo-7-(2-(1,2,3,4-tetraazoly l)acetylamino)-2H,7H,7aH-azetidino[2,1-b]1,3-thiazine-4-carboxylic acid, Oprea1_319479, Oprea1_496190, MLS001183701, CHEMBL172840, SCHEMBL4930576, CHEBI:94418, HMS2231F11, HMS3374P08, HMS5085D19, CID 2618, s5936, STK177242, AKOS001482982, AKOS021990220, SMR000677916, DB-046800, NS00007794, ST50901093, Cefazolin, Antibiotic for Culture Media Use Only, W-107209, Q27166276, (6S,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[[1-oxo-2-(1-tetrazolyl)ethyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-1,2,3,4-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-{[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl}-8-oxo-7-[(1H-tetrazol-1-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-(1H-Tetrazol-1-ylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid
Molecular formula: C₁₄H₁₄N₈O₄S₃
Empirical formula: C₁₄H₁₄N₈O₄S₃
Molecular weight: 454.5 g/mol
Exact mass: 454.03001
CAS number: 25953-19-9
PubChem CID: 2618
Canonical SMILES: CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
Isomeric SMILES: CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
InChI: InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)
InChIKey: MLYYVTUWGNIJIB-UHFFFAOYSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms: 29
Rings: 4
Aromatic rings: 2
Fraction sp³ carbons (Fsp3): 0.43
H-bond donors: 2
H-bond acceptors: 11 computed here · PubChem 12
Rotatable bonds: 7
TPSA (Å²): 156.1 computed here · PubChem 235
Formal charge: 0
XLogP3: -0.4 PubChem
Complexity: 740 PubChem
Stereocenters: 0 defined, 2 undefinedCIP: C16: undefined · C26: undefined
Double-bond geometry: None specified
Point group: C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

C37.00%
H3.10%
N24.65%
O14.08%
S21.17%

Isotope pattern

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P: -0.64 Crippen (Wildman and Crippen 1999)
log S (water solubility): -2.05 ESOL (Delaney 2004), log mol/L
Synthetic accessibility: 3.72 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

Molecular weight ≤ 500: 454.52
log P ≤ 5 (Crippen): -0.64
H-bond donors ≤ 5: 2
H-bond acceptors ≤ 10: 11

Breaks 1 of the four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

No GHS hazard classification was found in the sources.

Safety data sheets on the supplier’s page: AKos Consulting & Solutions, RR Scientific, MolCore.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

[1]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
[2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
[3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
[4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
·Literature on PubChem

Data last updated 2026-10-14.