Drug Information

General Information
Drug ID
DR00313
Drug Name
Cefadroxil
Synonyms
(6R,7R)-7-((R)-2-Amino-2-(p-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7beta-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,4-didehydrocepham-4-carboxylic acid; BL-S 578; BL-S578; CDX; Cefadroxil (JP15); Cefadroxil anhydrous; Cefadroxilo; Cefadroxilo [INN-Spanish]; Cefadroxilum; Cefadroxilum [INN-Latin]; Cephadroxil; Curisafe (TN); D-Cefadroxil; MJF-11567-3; S 578; S-578; Sumacef; Sumacef (TN)
Drug Type
Small molecular drug
Indication Gram-positive & negative bacteria infections [ICD11:1A00-1H0Z] Approved [1]
Therapeutic Class
Antibiotics
Structure
3D MOL 2D MOL
Formula
C16H17N3O5S
Canonical SMILES
CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O
InChI
InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
InChIKey
BOEGTKLJZSQCCD-UEKVPHQBSA-N
CAS Number
CAS 66592-87-8
Pharmaceutical Properties Molecular Weight 363.4 Topological Polar Surface Area 158
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
XLogP
-2.1
PubChem CID
47965
PubChem SID
103620148 ,103914339 ,104133801 ,104354273 ,10990583 ,11335584 ,11360823 ,11362958 ,11365520 ,11368082 ,11373871 ,11376244 ,11461795 ,11466462 ,11467582 ,11483750 ,11486123 ,11487903 ,11492081 ,11493918 ,121363085 ,124766005 ,14852631 ,16050996 ,24892921 ,25622160 ,34712894 ,46509128 ,47440185 ,47515253 ,47515254 ,47959665 ,48035040 ,48334422 ,48415709 ,49699087 ,50124273 ,57654040 ,75439952 ,7847323 ,7978892 ,8149235 ,85279381 ,87322627 ,90451718 ,9095 ,92125414 ,93576133 ,93576712 ,99301497
ChEBI ID
CHEBI:3479
TTD Drug ID
D0X9ZC
DT(s) Transporting This Drug MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [2]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [2]
MRP3 Transporter Info Multidrug resistance-associated protein 3 Substrate [2]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [2]
PEPT1 Transporter Info Peptide transporter 1 Substrate [3]
PEPT2 Transporter Info Peptide transporter 2 Substrate [4]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MRP1 Transporter Info Km =3.9 microM Human embryonic kidney cells (HEK293)-MRP1 [2]
MRP3 Transporter Info Km =2.5 microM Spodoptera frugiperda 21 (Sf21) cells-MRP3 [2]
MRP4 Transporter Info Km =0.25 microM Spodoptera frugiperda 21 (Sf21) cells-MRP4 [2]
PEPT1 Transporter Info Km =7.97 microM Human cervical cancer cell line (Hela)-PEPT1 [3]
PEPT2 Transporter Info Km =150.8 microM In vivo model (human) [4]
References
1 Cefadroxil was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Oral availability of cefadroxil depends on ABCC3 and ABCC4. Drug Metab Dispos. 2012 Mar;40(3):515-21.
3 High-affinity interaction of sartans with H+/peptide transporters. Drug Metab Dispos. 2009 Jan;37(1):143-9.
4 Species Differences in Human and Rodent PEPT2-Mediated Transport of Glycylsarcosine and Cefadroxil in Pichia Pastoris Transformants. Drug Metab Dispos. 2017 Feb;45(2):130-136.

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