Drug Information

General Information
Drug ID
DR00067
Drug Name
Aminohippuric acid
Synonyms
4-Aminohippuric acid; Aminohippurate; N-(4-Aminobenzoyl)glycine; PAH; PAHA; Para-aminohippurate
Drug Type
Small molecular drug
Indication Renal function tests [ICD11:MG02] Withdrawn [1]
Structure
3D MOL 2D MOL
Formula
C9H10N2O3
Canonical SMILES
C1=CC(=CC=C1C(=O)NCC(=O)O)N
InChI
InChI=1S/C9H10N2O3/c10-7-3-1-6(2-4-7)9(14)11-5-8(12)13/h1-4H,5,10H2,(H,11,14)(H,12,13)
InChIKey
HSMNQINEKMPTIC-UHFFFAOYSA-N
CAS Number
CAS 94-16-6
Pharmaceutical Properties Molecular Weight 194.19 Topological Polar Surface Area 92.4
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
XLogP
-0.9
PubChem CID
2148
PubChem SID
11112164 ,11335869 ,11361108 ,11364204 ,11366766 ,11369328 ,11372143 ,11374528 ,11377490 ,11462080 ,11466923 ,11468043 ,11485325 ,11486655 ,11489331 ,11490767 ,11492879 ,11495124 ,15322330 ,24890544 ,25621707 ,26612384 ,26679472 ,26748682 ,26748683 ,29221327 ,3135548 ,46507106 ,4656530 ,47365198 ,47440271 ,47515330 ,47515331 ,47885428 ,48035130 ,48185005 ,48415550 ,49661790 ,49698797 ,50064010 ,50939515 ,53787592 ,56366069 ,56463545 ,608583 ,73394 ,77615 ,8149888 ,8151459 ,840266
ChEBI ID
CHEBI:104011
TTD Drug ID
D04DLM
DT(s) Transporting This Drug ABCA8 Transporter Info ATP-binding cassette sub-family A member 8 Substrate [2]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [3]
MRP4 Transporter Info Multidrug resistance-associated protein 4 Substrate [4]
NPT3 Transporter Info Sodium-dependent phosphate transport protein 3 Substrate [5]
NPT4 Transporter Info Sodium-dependent phosphate transport protein 4 Substrate [6]
OAT1 Transporter Info Organic anion transporter 1 Substrate [7]
OAT3 Transporter Info Organic anion transporter 3 Substrate [8]
OATP1A2 Transporter Info Organic anion transporting polypeptide 1A2 Substrate [9]
Drug-Transporter Activity Data
Drug-Transporter Activity Data ABCA8 Transporter Info Km =5 microM Xenopus laevis oocytes-ABCA8 [2]
MRP1 Transporter Info Km =372 microM Human cervical cancer cell line (Hela)-MRP1 [3]
MRP2 Transporter Info Km =880 microM Human embryonic kidney cells (HEK293)-MRP2 [3]
MRP2 Transporter Info Km =2100 microM Madin-Darby canine kidney cells (MDCKII)-MRP2 [4]
MRP2 Transporter Info Km =5000 microM Spodoptera frugiperda (Sf9) cells-MRP2 [4]
MRP4 Transporter Info Km =160 microM Spodoptera frugiperda (Sf9) cells-MRP4 [4]
NPT3 Transporter Info Km =0.4 microM E.coli C43 (DE3) cells-NPT3 [5]
NPT4 Transporter Info Km =9560 microM Oocytes-NPT4 [6]
OAT1 Transporter Info Km =15.4 microM Chinese hamster ovary (CHO) cells-OAT1 [10]
OAT1 Transporter Info Km =5 microM Human cervical cancer cell line (Hela)-OAT1 [11]
OAT1 Transporter Info Km =20 microM Human embryonic kidney cells (HEK293)-OAT1 [12]
OAT1 Transporter Info Km =28 microM Human embryonic kidney cells (HEK293)-OAT1 [13]
OAT1 Transporter Info Km =8.5 microM Madin-Darby canine kidney (MDCK) cells-OAT1 [14]
OAT1 Transporter Info Km =8.9 microM Monkey kidney fibroblast-like cell (COS)7-OAT1 [15]
OAT1 Transporter Info Km =22 microM OK cells-OAT1 [16]
OAT1 Transporter Info Km =3.9 microM Oocytes-OAT1 [17]
OAT1 Transporter Info Km =4 microM Oocytes-OAT1 [18]
OAT1 Transporter Info Km =9.3 microM Oocytes-OAT1 [19]
OAT1 Transporter Info Km =20.1 microM Proximal tubule (S2) cells-OAT1 [20]
OAT3 Transporter Info Km =87.2 microM Oocytes-OAT3 [8]
SLC17A4 Transporter Info Km =700 microM E.coli C43 (DE3) cells-hNPT homologue [21]
References
1 National Center for Advancing Translational Science-Inxight: drug (Y79XT83BJ9)
2 Functional analysis of ABCA8, a new drug transporter. Biochem Biophys Res Commun. 2002 Oct 18;298(1):41-5.
3 ATP-dependent para-aminohippurate transport by apical multidrug resistance protein MRP2. Kidney Int. 2000 Apr;57(4):1636-42.
4 Contribution of multidrug resistance protein 2 (MRP2/ABCC2) to the renal excretion of p-aminohippurate (PAH) and identification of MRP4 (ABCC4) as a novel PAH transporter. J Am Soc Nephrol. 2004 Nov;15(11):2828-35.
5 Wide expression of type I Na+-phosphate cotransporter 3 (NPT3/SLC17A2), a membrane potential-driven organic anion transporter. Am J Physiol Cell Physiol. 2015 Jul 15;309(2):C71-80.
6 Human sodium phosphate transporter 4 (hNPT4/SLC17A3) as a common renal secretory pathway for drugs and urate. J Biol Chem. 2010 Nov 5;285(45):35123-32.
7 Interactions of human organic anion transporter 1 (hOAT1) with substances associated with forensic toxicology. Leg Med (Tokyo). 2011 Jul;13(4):180-5.
8 Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86.
9 Characterization and identification of steroid sulfate transporters of human placenta. Am J Physiol Endocrinol Metab. 2003 Feb;284(2):E390-8.
10 Cytotoxicity of antiviral nucleotides adefovir and cidofovir is induced by the expression of human renal organic anion transporter 1. J Am Soc Nephrol. 2000 Mar;11(3):383-93.
11 Cloning of the human kidney PAH transporter: narrow substrate specificity and regulation by protein kinase C. Am J Physiol. 1999 Feb;276(2):F295-303.
12 Expression of organic anion transporter 2 in the human kidney and its potential role in the tubular secretion of guanine-containing antiviral drugs. Drug Metab Dispos. 2012 Mar;40(3):617-24.
13 Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1. Biochem Pharmacol. 2005 Oct 1;70(7):1104-13.
14 Stoichiometry of organic anion/dicarboxylate exchange in membrane vesicles from rat renal cortex and hOAT1-expressing cells. Am J Physiol Renal Physiol. 2003 Oct;285(4):F775-83.
15 Interaction of cysteine conjugates with human and rabbit organic anion transporter 1. J Pharmacol Exp Ther. 2003 Feb;304(2):560-6.
16 Uraemic toxins induce proximal tubular injury via organic anion transporter 1-mediated uptake. Br J Pharmacol. 2002 Jan;135(2):555-63.
17 Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1. J Pharmacol Exp Ther. 2001 Nov;299(2):741-7.
18 The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1. Mol Pharmacol. 1999 Sep;56(3):570-80.
19 Molecular cloning and functional expression of a multispecific organic anion transporter from human kidney. Am J Physiol. 1999 Jan;276(1):F122-8.
20 Characterization of organic anion transport inhibitors using cells stably expressing human organic anion transporters. Eur J Pharmacol. 2001 May 11;419(2-3):113-20.
21 A Na+-phosphate cotransporter homologue (SLC17A4 protein) is an intestinal organic anion exporter. Am J Physiol Cell Physiol. 2012 Jun 1;302(11):C1652-60.

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