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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16N2O6S2
Molecular Weight 396.438
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALOTHIN

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC3=CC=CS3)C(O)=O

InChI

InChIKey=XIURVHNZVLADCM-IUODEOHRSA-N
InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H16N2O6S2
Molecular Weight 396.438
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cephalothin is a first generation, semisynthetic analogue of natural cephalosporin antibiotic. The in-vitro bactericidal action of Cephalothin results from inhibition of cell-wall synthesis. In general, Cephalothin has higher activity against Gram positive than Gram negative organisms. Cephalothin is primarily indicated in conditions like bone and joint infection, genitourinary tract infections, respiratory tract infections, soft tissue and skin infections and others. The severe or irreversible adverse effects of Cephalothin, which give rise to further complications, include nephrotoxicity, hemolytic anemia. Cephalothin produces potentially life-threatening effects, which include anaphylaxis, serum sickness syndrome. The symptomatic adverse reactions produced by Cephalothin are: rashes, urticaria, allergic reactions, thrombophlebitis, pain at injection site. Co-administration of diuretics, such as furanthril, ethacrynic acid and nephrotoxic antibiotics may increase the risk of renal damage. Reciprocal inactivation could be observed during in vitro mixing of Cephalothin with aminoglycosides.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.41 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
KEFLIN
Curative
KEFLIN
Curative
KEFLIN
Curative
KEFLIN
Curative
KEFLIN
Curative
KEFLIN

Cmax

ValueDoseCo-administeredAnalytePopulation
20.8 μg/mL
3 g single, intravenous
CEPHALOTHIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
25.2 μg × h/mL
3 g single, intravenous
CEPHALOTHIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
28 min
3 g single, intravenous
CEPHALOTHIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
The usual dosage range is 500 mg to 1 g of cefalotin every four to six hours. In severe infections, this may be increased by giving the injections every four hours or, when the desired response is not obtained, by raising the dose to 1 g. In lifethreatening infections, in patients with normal renal function, doses up to 2 g every four hours may be required.
Route of Administration: Other
In Vitro Use Guide
Cephalothin was very effective in vitro against staphylococcal isolates, with an MIC90 of 0.12 ug/mL. The cephalothin MIC90 for E.coli was 64 ug/mL.
Substance Class Chemical
Record UNII
R72LW146E6
Record Status Validated (UNII)
Record Version