Cephapirin

Details

• Internal ID: 674eef74-536b-4866-89fd-e70ed43a0c56
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > N-acyl-alpha amino acids and derivatives
• IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• InChI: InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
• InChI Key: UQLLWWBDSUHNEB-CZUORRHYSA-N
• Popularity: 917 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₇N₃O₆S₂
• Molecular Weight: 423.50 g/mol
• Exact Mass: 423.05587762 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): 0.48
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• Cefapirin
• Cephapirine
• Cefaprin
• 21593-23-7
• Cefadyl
• Cefapirina
• Cefapirine
• Cefapirinum
• CEPR
• Cefapirine [INN-French]
• Cefapirinum [INN-Latin]
• Cefapirina [INN-Spanish]
• CHEBI:554446
• Cefatrexyl
• Ambrocef
• Cefatrex
• 7-(2-(4-Pyridylthio)acetamido)cephalosporanic acid
• HSDB 3215
• 89B59H32VN
• EINECS 244-466-5
• BRN 1095157
• UNII-89B59H32VN
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridinylthio)acetyl)amino)-, (6R-trans)-
• DTXSID9022784
• Cefa
• Cefaprin sodium
• (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
• (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• 3-(Hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamidol-5-thia-1-azabicyclo(4.2.0)oct-2-en-2carbonsaeure acetat
• 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, acetate (ester)
• Cephalosporanic acid, 7-(2-(4-pyridylthio)acetamido)-
• Cefapirine (INN-French)
• Cefapirinum (INN-Latin)
• Cefapirina (INN-Spanish)
• Cefapirin [INN:BAN]
• ANTIBIOTIC BL-P1322
• Cefapirin (BAN)
• Metricure (TN)
• (6R,7R)-3-(acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-3-(HYDROXYMETHYL)-8-OXO-7-(2-(4-PYRIDYLTHIO)ACETAMIDO)-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE ACETATE (ESTER)
• (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R,7R)-3-acetoxymethyl-7-[(pyridin-4-ylsulfanyl)acetamido]-3,4-didehydrocepham-4-carboxylic acid
• NSC179171
• 24356-60-3
• Cefa-Lak
• Cefa -ak
• (6R,7R)-3-(acetoxymethyl)-8-oxo-7-(((pyridin-4-ylsulfanyl)acetyl)amino)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• (6R,7R)-3-acetoxymethyl-7-((pyridin-4-ylsulfanyl)acetamido)-3,4-didehydrocepham-4-carboxylic acid
• Spectrum_000112
• CEFAPIRIN [INN]
• CEPHAPIRIN [MI]
• CEFAPIRIN [HSDB]
• Prestwick0_000851
• Prestwick1_000851
• Prestwick2_000851
• Spectrum2_000103
• Spectrum3_000333
• Spectrum4_000270
• Spectrum5_000671
• CEPHAPIRIN [VANDF]
• Epitope ID:116226
• CEFAPIRIN [WHO-DD]
• SCHEMBL3205
• CHEMBL1599
• Lopac0_000279
• BSPBio_001965
• KBioGR_000740
• KBioSS_000552
• DivK1c_000042
• SPBio_000086
• SPBio_002782
• DTXCID602784
• GTPL12191
• KBio1_000042
• KBio2_000552
• KBio2_003120
• KBio2_005688
• KBio3_001185
• NINDS_000042
• UQLLWWBDSUHNEB-CZUORRHYSA-N
• HY-A0153
• BDBM50370592
• AKOS015896499
• DB01139
• IDI1_000042
• (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-ylthio)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• SBI-0050267.P004
• CS-0017478
• C06896
• D07636
• EN300-25916814
• Q549803
• J-014163
• 7-(alpha-(4-PYRIDYLTHIO)ACETAMIDO)CEPHALOSPORANIC ACID
• 7-(.ALPHA.-(4-PYRIDYLTHIO)ACETAMIDO)CEPHALOSPORANIC ACID
• (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid
• (6R,7R)-3-(acetoxymethyl)-8-oxo-7-[[2-(4-pyridylsulfanyl)acetyl]amino]-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-[(acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-, (6R,7R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4712	47.12%
Caco-2	-	0.8785	87.85%
Blood Brain Barrier	-	1.0000	100.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.4553	45.53%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8436	84.36%
OATP1B3 inhibitior	+	0.9348	93.48%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8399	83.99%
BSEP inhibitior	+	0.6227	62.27%
P-glycoprotein inhibitior	-	0.9167	91.67%
P-glycoprotein substrate	-	0.6244	62.44%
CYP3A4 substrate	+	0.5924	59.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8812	88.12%
CYP3A4 inhibition	-	0.8003	80.03%
CYP2C9 inhibition	-	0.7348	73.48%
CYP2C19 inhibition	-	0.7075	70.75%
CYP2D6 inhibition	-	0.8753	87.53%
CYP1A2 inhibition	-	0.7695	76.95%
CYP2C8 inhibition	-	0.5717	57.17%
CYP inhibitory promiscuity	+	0.5917	59.17%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5586	55.86%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9615	96.15%
Skin irritation	-	0.7561	75.61%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5713	57.13%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.5828	58.28%
skin sensitisation	-	0.8276	82.76%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	+	0.8490	84.90%
Acute Oral Toxicity (c)	IV	0.6182	61.82%
Estrogen receptor binding	+	0.7509	75.09%
Androgen receptor binding	-	0.6824	68.24%
Thyroid receptor binding	-	0.6001	60.01%
Glucocorticoid receptor binding	-	0.4897	48.97%
Aromatase binding	-	0.5200	52.00%
PPAR gamma	+	0.5204	52.04%
Honey bee toxicity	-	0.8654	86.54%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.8999	89.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.56%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.46%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	93.24%	93.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.46%	85.14%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	90.29%	81.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.82%	99.23%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	87.17%	87.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.14%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.20%	99.17%
CHEMBL4578	Q14680	Maternal embryonic leucine zipper kinase	84.20%	81.58%
CHEMBL255	P29275	Adenosine A2b receptor	84.16%	98.59%
CHEMBL3891	P07384	Calpain 1	80.94%	93.04%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 30699
• LOTUS: LTS0031469
• wikiData: Q549803