Cefazolin

Details

• Internal ID: 18ec1ae7-3443-4758-9240-f16eb20e01d8
• Taxonomy: Organoheterocyclic compounds > Lactams > Beta lactams > Cephalosporins
• IUPAC Name: (6R,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
• SMILES (Canonical): CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=NN=N4)SC2)C(=O)O
• SMILES (Isomeric): CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](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)/t9-,12-/m1/s1
• InChI Key: MLYYVTUWGNIJIB-BXKDBHETSA-N
• Popularity: 13,116 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₄N₈O₄S₃
• Molecular Weight: 454.50 g/mol
• Exact Mass: 454.03001448 g/mol
• Topological Polar Surface Area (TPSA): 235.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.64
• H-Bond Acceptor: 12
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 25953-19-9
• Cephazolin
• Cefazoline
• Cephamezine
• Cephazoline
• Cefamezin
• Cephazolidin
• Cefazolin acid
• Cefazolina
• Cefazolinum
• Elzogram
• CEZ
• Cefazoline [INN-French]
• Cefazolinum [INN-Latin]
• Cefazolina [INN-Spanish]
• Kefzol
• HSDB 3213
• CHEBI:474053
• UNII-IHS69L0Y4T
• EINECS 247-362-8
• IHS69L0Y4T
• BRN 4169371
• (6R,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
• DTXSID2022753
• J01DB04
• Cefazolin [USP:INN:BAN]
• DTXCID302753
• EC 247-362-8
• Cefazina
• Firmacef
• Liviclina
• Atirin
• Acef
• (6R,7R)-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
• NCGC00159465-02
• Cefazoline (INN-French)
• Cefazolinum (INN-Latin)
• Cefazolina (INN-Spanish)
• CEFAZOLIN (MART.)
• CEFAZOLIN [MART.]
• CEFAZOLIN (USP-RS)
• CEFAZOLIN [USP-RS]
• SK&F-41558
• Cefazolin (USP:INN:BAN)
• (6R,7R)-7-(2-(1H-tetrazol-1-yl)acetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CEFAZOLIN (USP MONOGRAPH)
• CEFAZOLIN [USP MONOGRAPH]
• Cephamezine;Cephazoline
• Cefazolin (USP)
• (6R,7R)-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
• (6R,7R)-7-(2-(1H-tetrazol-1-yl)acetamido)-3-((5-methyl-1,3,4-thiadiazol-2-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• SMR000387025
• CAS-25953-19-9
• NSC291561
• Cefazolin acid,(S)
• (6R,7R)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(2-(1H-tetrazol-1-yl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• (6R-trans)-3-(((5-Methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1H-tetrazol-1-yl)acetyl)-amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• 7-(1-(1H-)-Tetrazolylacetamido)-3-(2-(5-methyl-1,3,4-thiadiazolyl)thiomethyl)delta3-cephem-4-carboxylic acid
• Spectrum_000106
• CEFAZOLIN [INN]
• CEFAZOLIN [MI]
• CEFAZOLIN [HSDB]
• Prestwick0_000736
• Prestwick1_000736
• Prestwick2_000736
• Prestwick3_000736
• Spectrum2_001140
• Spectrum3_000330
• Spectrum4_000267
• Spectrum5_000665
• CEFAZOLIN [VANDF]
• Cefazolinfor culture media
• Epitope ID:116197
• CEFAZOLIN [WHO-DD]
• SCHEMBL2841
• CHEMBL1435
• Lopac0_000274
• BSPBio_000692
• BSPBio_001939
• KBioGR_000734
• KBioSS_000546
• MLS001032060
• MLS001049010
• DivK1c_000014
• SPBio_001039
• SPBio_002631
• BPBio1_000762
• GTPL10935
• KBio1_000014
• KBio2_000546
• KBio2_003114
• KBio2_005682
• KBio3_001159
• MLYYVTUWGNIJIB-BXKDBHETSA-N
• NINDS_000014
• HMS2268D15
• 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]-, (6R,7R)-
• HY-B1892
• Tox21_111691
• BDBM50370587
• s5936
• AKOS015962265
• Tox21_111691_1
• DB01327
• SDCCGSBI-0050262.P005
• IDI1_000014
• NCGC00022653-09
• (6R,7R)-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
• 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-7beta-[(1H-tetrazol-1-ylacetyl)amino]-3,4-didehydrocepham-4-carboxylic acid
• 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-yl)acetyl)amino)-, (6R-trans)-
• 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)acetamido)-
• AC-16010
• BS-52943
• Cefazolin 1000 microg/mL in Acetonitrile
• SBI-0050262.P004
• CS-0013954
• 7-(1-(1H-)-TETRAZOLYLACETAMIDO)-3-
• C06880
• D02299
• F87674
• EN300-6731073
• A818105
• Q415739
• W-107209
• (6R, 7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2- yl)thio]methyl]-8-oxo-7-[[1H-tetrazol-1- yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2- ene-2-carboxylic acid
• (6R,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;Cefazolin acid
• (6R,7R)-3-[[(5-Methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-[2-(1H-tetrazol-1-yl)acetamido]5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 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-YL)ACETYL)AMINO)-(6R-TRANS)
• Cefazolin; (6R,7R)-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; (6R,7R)-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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7844	78.44%
Caco-2	-	0.8978	89.78%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6101	61.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9306	93.06%
OATP1B3 inhibitior	+	0.9295	92.95%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5660	56.60%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.6191	61.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8863	88.63%
CYP3A4 inhibition	-	0.9377	93.77%
CYP2C9 inhibition	-	0.8746	87.46%
CYP2C19 inhibition	-	0.8363	83.63%
CYP2D6 inhibition	-	0.9178	91.78%
CYP1A2 inhibition	-	0.8949	89.49%
CYP2C8 inhibition	-	0.6390	63.90%
CYP inhibitory promiscuity	-	0.6362	63.62%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4944	49.44%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9578	95.78%
Skin irritation	-	0.7562	75.62%
Skin corrosion	-	0.9212	92.12%
Ames mutagenesis	-	0.5254	52.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6857	68.57%
Micronuclear	+	0.9500	95.00%
Hepatotoxicity	+	1.0000	100.00%
skin sensitisation	-	0.8230	82.30%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.5712	57.12%
Estrogen receptor binding	-	0.8682	86.82%
Androgen receptor binding	-	0.7574	75.74%
Thyroid receptor binding	-	0.5523	55.23%
Glucocorticoid receptor binding	-	0.5959	59.59%
Aromatase binding	+	0.5331	53.31%
PPAR gamma	+	0.5489	54.89%
Honey bee toxicity	-	0.8490	84.90%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9282	92.82%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293235	P02545	Prelamin-A/C	891.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.15%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.11%	98.95%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	95.82%	87.67%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	95.68%	81.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	94.64%	93.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.20%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.76%	99.23%
CHEMBL261	P00915	Carbonic anhydrase I	92.67%	96.76%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.18%	85.14%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.04%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.54%	95.56%
CHEMBL3769292	Q9H773	dCTP pyrophosphatase 1	86.16%	94.40%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.78%	97.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.58%	96.90%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 33255
• LOTUS: LTS0145921
• wikiData: Q415739