HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

(6R,7R)-7-[[(2R)-2-azaniumyl-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HCID 6560168
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
15686-71-2
Standard SMILES
CC1=C(C(=O)[O-])N2C(=O)[C@@H](NC(=O)[C@H]([NH3+])c3ccccc3)[C@H]2SC1
InChIKey
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N
Molecular formula
C16H17N3O4S
Average molar mass
347.4 g/mol
Monoisotopic mass
347.09397721

Overview

Cephalexin is the first of the first generation cephalosporins. This antibiotic contains a beta lactam and a dihydrothiazide. Cephalexin is used to treat a number of susceptible bacterial infections through inhibition of cell wall synthesis. Cephalexin was approved by the FDA on 4 January 1971.

Names & identifiers

Preferred name
(6R,7R)-7-[[(2R)-2-azaniumyl-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
IUPAC
(6R,7R)-7-[[(2R)-2-azaniumyl-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
English name
Cephalexin
Molecular formula
C16H17N3O4S
Molecular weight
347.39

Names & synonyms

CEFALEXINCEFALEXIN SODIUMoroxinCEPOREXCEPHALEXINEcexs6437syncloracefkeforal

Database identifiers

CAS
15686-71-2
PubChem CID
6560168

Properties

Computed structural properties

XLogP
1.3
Topological polar surface area
142 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
3
Heavy atoms
24
Formal charge
0
Complexity
595

Experimental & physicochemical properties

Solubility · 2 items

10mg/mL

2.97e-01 g/L

Melting Point326.8 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
196 · 196-198°C
alpha
20 · [α]D20 +144~+158° (c=0.5, H2O) (Calculated on dehydrous basis)
Boiling point
727.4 · 727.4±60.0 °C(Predicted)
Density
1.304 · 1.3040 (rough estimate)
refractive index
1.632 · 1.6320 (estimate)
storage temp.
2 · Keep in dark place,Inert atmosphere,2-8°C
solubility
4 OH · NH4OH 1 M: 50 mg/mL, clear, yellow
pka
5.2 · 5.2, 7.3(at 25℃)
form
Solid
color
White to light yellow
PH
5 g/l, · pH (5g/l, 25℃) 3.5~5.5
Water Solubility
12.5 g/L · 12.5g/L(25 ºC)
Merck
13 · 13,1986
BCS Class
4 · 4
Major Application
forensics and toxicologypharmaceutical (small molecule)
InChI
1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
InChIKey
AVGYWQBCYZHHPN-CYJZLJNKSA-N
SMILES
N[C@@H](C(N[C@@H]1C(N2[C@]1([H])SCC(C)=C2C(O)=O)=O)=O)C3=CC=CC=C3
CAS DataBase Reference
15686 · 15686-71-2(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
cephalexin
FDA UNII
5 SFF1W6677 · 5SFF1W6677
NCI Drug Dictionary
cephalexin
ATC code
1 DB01 · J01DB01
EPA Substance Registry System
5 · 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-, (6R,7R)- (15686-71-2)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Protein binding
15 % · 15%
Excreted unchanged in urine
80 · 80-90%
Volume of distribution
0.35 · 0.35(L/kg)
Biological half-life
1 · 1 / 16
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
317 · H317-H334
Precautionary statements
261 · P261-P272-P280-P284-P302+P352-P333+P313
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn
Risk Statements
42 · 42/43
Safety Statements
22 · 22-36/37-45
WGK Germany
3 · 3
RTECS
350000 · XI0350000
HS Code
29419000 · 29419000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
1 Skin · Resp. Sens. 1Skin Sens. 1
Hazardous Substances Data
15686 · 15686-71-2(Hazardous Substances Data)
Toxicity
14 mg/kg/D:GIT · TDLo orl-hmn: 14 mg/kg/D:GIT AACHAX -,361,68

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
rtecs
XI0350000
hs_code
29419000
Toxicity
TDLo orl-hmn: 14 mg/kg/D:GIT AACHAX -,361,68
risk_code
42/43
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
Xn
safety_code
22-36/37-45
Storage Class
11 - Combustible Solids
Hazard statements
H317-H334
Hazard Classifications
Resp. Sens. 1Skin Sens. 1
Precautionary statements
P261-P272-P280-P284-P302+P352-P333+P313
Hazardous Substances Data
15686-71-2(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Protein BindingCephalexin is 10-15% bound to serum proteins including serum albumin.
Pharmacodynamics · 1 item

Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic. It is one of the most widely prescribed antibiotics, often used for the treatment of superficial infections that result as complications of minor wounds or lacerations. It is effective against most gram-positive bacteria through its inihibition of the cross linking reaction between N-acetyl muramicacid and N-acetylglucosamine in the cell wall, leading to cell lysis.

Mechanism of Action · 1 item

Cephalexin is a first generation cephalosporin antibiotic. Cephalosporins contain a beta lactam and dihydrothiazide. Unlike penicillins, cephalosprins are more resistant to the action of beta lactamase. Cephalexin inhibits bacterial cell wall synthesis, leading breakdown and eventualy cell death.

Biological Half-LifeThe half life of cephalexin is 49.5 minutes in a fasted state and 76.5 minutes with food though these times were not significantly different in the study.
Metabolism/MetabolitesCephalexin is not metabolized in the body.
Absorption, Distribution and Excretion · 4 items

Well absorbed from the upper gastrointestinal tract with nearly 100% oral bioavailability. Cephalexin is not absorbed in the stomach but is absorbed in the upper intestine. Patients taking 250mg of cephalexin reach a maximum plasma concentration of 7.7mcg/mL and patients taking 500mg reach 12.3mcg/mL.

Cephalexin is over 90% excreted in the urine after 6 hours by glomerular filtration and tubular secretion with a mean urinary recovery of 99.3%. Cephalexin is unchanged in the urine.

5.2-5.8L.

Clearance from one subject was 376mL/min.

Cellular LocationsExtracellular
Applications · 4 items

DescriptionCephalexin is a cephalosporin antibiotic that is used to examine the impact of binding, expression, and inhibition of PBP3 as well as additional penicillin-binding proteins (PBPs) on the cell wall during bacterial mucopeptide synthesis. Cephalexin is used for the treatment of infection-causing bacteria that may induce ear, respiratory, urinary tract, and skin infections. Bacteria that are defenseless against Cephalexin may include Streptococcus pneumonia, Staphylococcus aureus, E. coli, and Haemophilus influenza. Cephalexin is also referred to as Keflex (brand name), and it does not relieve viral infections such as flu or colds.

UsesCephalexin is administered to minimize the development of bacteria that are resistant to drugs. To maintain the overall effectiveness of Cephalexin, the drug should be prescribed as a treatment for infections that can be attributed to bacteria. The availability of susceptibility and culture information should be put into consideration while making modifications to antibacterial therapy. The absence of such information may be backed by susceptibility and epidemiology patterns to influence verifiable adoption of treatment. In some cases, Cephalexin is used for the treatment of patients who are allergic to penicillin and may have a heart condition at the time when they are undergoing a procedure on their respiratory tract, to inhibit the development of infection on their heart valves.

DescriptionUse of the ampicillin-type side chain conveys oral activity to cephalexin. Whereas it no longer has an activating side chain at C-3 and, as a consequence, is somewhat less potent, it does not undergo metabolic deactivation and, thus, maintains potency. It is rapidly and completely absorbed from the GI tract and has become quite popular. Somewhat puzzling is the fact that the use of the ampicillin side chain in the cephalosporins does not result in a comparable shift in antimicrobial spectrum. Cephalexin, like the other first-generation cephalosporins is active against many Gram-positive aerobic cocci but is limited against Gram-negative bacteria. It is a widely used drug, particularly against Gram-negative bacteria causing urinary tract infections, Gram-positive infections (Staphyl ococcus aureus, Streptococcus pneumoni ae and Streptococcus pyogenes) of soft tissues, pharyngitis, and minor wounds.

UsesAntibacterial.

Upstream & downstream products

Upstream raw materials

Penicillin G potassium saltHydrochloric acidMethyl acetoacetateZINC

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]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
湖北辰心化工有限公司18696113233 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Syntechem Co.,Ltd[email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
合肥天健化工有限公司551-65418679 15856988503;15837135945 · [email protected]
南京美博生物科技有限公司025-58619198 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海遐瑞医药科技有限公司+86 21 61551611
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海创赛科技有限公司400-6087598 15021221957 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
Alfa Chemistry1-516-6625404 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
北京诺其雅盛生物科技有限公司4000-819-385 010-62329685 13718666987
上海波以尔化工有限公司021-50182298 021-50180596 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
BOC Sciences16314854226 · [email protected]
南京艾比克斯生化科技有限公司025-87193546 18652950785 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]
哈药集团制药总厂0451-86671777
Additional notes · 1 item

DefinitionChEBI: A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and G am-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.

Related reactions

0 records
New reaction record

No reaction records under the current filter.

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes