U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H17ClN2
Molecular Weight 344.8375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOTRIMAZOLE

SMILES

c1ccc(cc1)C(c2ccccc2)(c3ccccc3Cl)n4ccnc4

InChI

InChIKey=VNFPBHJOKIVQEB-UHFFFAOYSA-N
InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H

HIDE SMILES / InChI

Molecular Formula C22H17ClN2
Molecular Weight 344.8375
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018052Orig1s032lbl.pdf

Clotrimazole is an anti-fungal medicine indicated for the treatment of vaginal yeast infections and tinea. It can be used either in combination with other drugs (betamethasone dipropionate) or alone, in form of topical or vaginal cream. The drug exerts its action by inhibiting lanosterol demethylase thereby affecting the growth of fungi.

Originator

Curator's Comment:: # Bayer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
19.7 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
GYNE-LOTRIMIN

Approved Use

To treat vaginal yeast infections.

Launch Date

1.96473602E11
Curative
LOTRISONE

Approved Use

LOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older.

Launch Date

4.58265592E11
Curative
LOTRISONE

Approved Use

LOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older.

Launch Date

4.58265592E11
Curative
LOTRISONE

Approved Use

LOTRISONE cream contains a combination of clotrimazole, an azole antifungal, and betamethasone dipropionate, a corticosteroid, and is indicated for the topical treatment of symptomatic inflammatory tinea pedis, tinea cruris, and tinea corporis due to Epidermophyton floccosum, Trichophyton mentagrophytes, and Trichophyton rubrum in patients 17 years and older.

Launch Date

4.58265592E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.3 μM
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
12.59 μM × h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.99 h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOTRIMAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
10 mg 5 times / day multiple, oral
Recommended
Dose: 10 mg, 5 times / day
Route: oral
Route: multiple
Dose: 10 mg, 5 times / day
Sources:
unhealthy, 33 years (range: 22 - 43 years)
n = 20
Health Status: unhealthy
Condition: Oral Candidiasis
Age Group: 33 years (range: 22 - 43 years)
Sex: M+F
Population Size: 20
Sources:
Disc. AE: Nausea, Taste abnormality...
AEs leading to
discontinuation/dose reduction:
Nausea (2 patients)
Taste abnormality (2 patients)
Sources:
500 mg single, vaginal
Highest studied dose
Dose: 500 mg
Route: vaginal
Route: single
Dose: 500 mg
Co-administed with::
lactic acid
Sources:
unhealthy, adult
n = 89
Disc. AE: Vulvovaginal burning sensation...
AEs leading to
discontinuation/dose reduction:
Vulvovaginal burning sensation (1 patient)
Sources:
500 mg single, vaginal
Highest studied dose
Dose: 500 mg
Route: vaginal
Route: single
Dose: 500 mg
Co-administed with::
lactic acid
Sources:
unhealthy, adult
Disc. AE: Vulvovaginal pruritus...
AEs leading to
discontinuation/dose reduction:
Vulvovaginal pruritus (1 patient)
Sources:
50 mg 1 times / day multiple, vaginal
Dose: 50 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p. 5
unhealthy, adult
n = 323
Health Status: unhealthy
Age Group: adult
Sex: F
Population Size: 323
Sources: Page: p. 5
Disc. AE: Vaginal irritation, Spotting vaginal...
AEs leading to
discontinuation/dose reduction:
Vaginal irritation (1 patient)
Spotting vaginal (1 patient)
Sources: Page: p. 5
AEs

AEs

AESignificanceDosePopulation
Nausea 2 patients
Disc. AE
10 mg 5 times / day multiple, oral
Recommended
Dose: 10 mg, 5 times / day
Route: oral
Route: multiple
Dose: 10 mg, 5 times / day
Sources:
unhealthy, 33 years (range: 22 - 43 years)
n = 20
Health Status: unhealthy
Condition: Oral Candidiasis
Age Group: 33 years (range: 22 - 43 years)
Sex: M+F
Population Size: 20
Sources:
Taste abnormality 2 patients
Disc. AE
10 mg 5 times / day multiple, oral
Recommended
Dose: 10 mg, 5 times / day
Route: oral
Route: multiple
Dose: 10 mg, 5 times / day
Sources:
unhealthy, 33 years (range: 22 - 43 years)
n = 20
Health Status: unhealthy
Condition: Oral Candidiasis
Age Group: 33 years (range: 22 - 43 years)
Sex: M+F
Population Size: 20
Sources:
Vulvovaginal burning sensation 1 patient
Disc. AE
500 mg single, vaginal
Highest studied dose
Dose: 500 mg
Route: vaginal
Route: single
Dose: 500 mg
Co-administed with::
lactic acid
Sources:
unhealthy, adult
n = 89
Vulvovaginal pruritus 1 patient
Disc. AE
500 mg single, vaginal
Highest studied dose
Dose: 500 mg
Route: vaginal
Route: single
Dose: 500 mg
Co-administed with::
lactic acid
Sources:
unhealthy, adult
Spotting vaginal 1 patient
Disc. AE
50 mg 1 times / day multiple, vaginal
Dose: 50 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p. 5
unhealthy, adult
n = 323
Health Status: unhealthy
Age Group: adult
Sex: F
Population Size: 323
Sources: Page: p. 5
Vaginal irritation 1 patient
Disc. AE
50 mg 1 times / day multiple, vaginal
Dose: 50 mg, 1 times / day
Route: vaginal
Route: multiple
Dose: 50 mg, 1 times / day
Sources: Page: p. 5
unhealthy, adult
n = 323
Health Status: unhealthy
Age Group: adult
Sex: F
Population Size: 323
Sources: Page: p. 5
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
yes [IC50 0.00315 uM]
yes [IC50 0.00822 uM]
yes [IC50 0.1 uM]
yes [IC50 0.745 uM]
yes [IC50 2.3 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes [IC50 >10 uM]
yes
yes
yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Swelling-induced K(+) fluxes in vascular smooth muscle cells are mediated by charybdotoxin-sensitive K(+) channels.
2001
[Vulvovaginal candidiasis in childhood--diagnostic and therapeutic results].
2001
Topical treatment for vaginal candidiasis (thrush) in pregnancy.
2001
Drug sensitivity of Candida yeast isolated from patients with allergic diseases.
2001 Apr
Tinea incognito caused by trichophyton mentagrophytes -- a case report.
2001 Dec
Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine.
2001 Dec
Development of a mucoadhesive dosage form for vaginal administration.
2001 Jul
[Therapeutic efficacy of a topical tolnaftate preparation in guinea pig model of tinea pedis].
2001 Jun
Outcome of 22 cases of perforated tympanic membrane caused by otomycosis.
2001 Nov
Otomycosis in Nigeria: treatment with mercurochrome.
2001 Nov
[How I treat ... sickle cell anemia: current therapies].
2001 Oct
Sertaconazole: in-vitro antifungal activity against vaginal and other superficial yeast isolates.
2001 Oct
In vitro activity of 6 antifungal agents on candida species isolated as causative agents from vaginal and other clinical specimens.
2001 Oct
Novel effects of minocycline on Ca(2+)-dependent Cl(-) secretion in human airway epithelial Calu-3 cells.
2001 Oct 15
Angiotensin II type AT(2) receptor mRNA expression and renal vasodilatation are increased in renal failure.
2001 Sep
Use of topical clotrimazole in human keratomycosis.
2001 Sep-Oct
Orphan nuclear receptor binding site in the human inducible nitric oxide synthase promoter mediates responsiveness to steroid and xenobiotic ligands.
2002
Interventions for treating oral candidiasis for patients with cancer receiving treatment.
2002
Clinical comparison of the efficacy and tolerability of once daily Canesten with twice daily Nizoral (clotrimazole 1% cream vs. ketoconazole 2% cream) during a 28-day topical treatment of interdigital tinea pedis.
2002 Apr
Do azoles and chloroquine share similar mechanisms of antimalarial action?
2002 Apr
Crystallization and preliminary crystallographic analysis of a novel cytochrome P450 from Mycobacterium tuberculosis.
2002 Apr
Cytochrome P450 3A conjugation to ubiquitin in a process distinct from classical ubiquitination pathway.
2002 Apr
Dehydration response of sickle cells to sickling-induced Ca(++) permeabilization.
2002 Apr 1
Translation initiation and its deregulation during tumorigenesis.
2002 Apr 8
Clotrimazole-triiodide ion association as an ion exchanger for a triiodide ion-selective electrode.
2002 Feb
Contribution of cytochrome P450 metabolites to bradykinin-induced vasodilation in endothelial NO synthase deficient mouse hearts.
2002 Feb
Activation of ion secretion via proteinase-activated receptor-2 in human colon.
2002 Feb
Characterization of basolateral K+ channels underlying anion secretion in the human airway cell line Calu-3.
2002 Feb 1
Modulation of mouse Paneth cell alpha-defensin secretion by mIKCa1, a Ca2+-activated, intermediate conductance potassium channel.
2002 Feb 1
Arginine supplementation of sickle transgenic mice reduces red cell density and Gardos channel activity.
2002 Feb 15
Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression.
2002 Feb 28
Topical antifungal drug products for over-the-counter human use; amendment of final monograph. Final rule.
2002 Feb 8
Clotrimazole binds to heme and enhances heme-dependent hemolysis: proposed antimalarial mechanism of clotrimazole.
2002 Feb 8
Comparison of two methods for antifungal susceptibility testing of Trichophyton rubrum.
2002 Jan
Development of a topical suspension containing three active ingredients.
2002 Jan
Perianal ulcerations from topical steroid use.
2002 Jan
A pilot study evaluating the safety and microbiologic efficacy of an economically viable antimicrobial lozenge in patients with head and neck cancer receiving radiation therapy.
2002 Jan
Adenovirus vector-mediated reporter system for in vivo analyses of human CYP3A4 gene activation.
2002 Jan
Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine.
2002 Jan 1
Differential pulse polarographic determination of clotrimazole after derivatization with Procion Red HE-3B.
2002 Jan 1
Topical antibiotic, antifungal, and antiseptic solutions decrease ciliary activity in nasal respiratory cells.
2002 Jan-Feb
Clotrimazole/betamethasone diproprionate: a review of costs and complications in the treatment of common cutaneous fungal infections.
2002 Jan-Feb
K+ currents generated by NMDA receptor activation in rat hippocampal pyramidal neurons.
2002 Jun
The flavonol quercetin activates basolateral K(+) channels in rat distal colon epithelium.
2002 Mar
Effect of antifungal azoles on the heme detoxification system of malarial parasite.
2002 Mar
Inhibition of cytochromes P450 by antifungal imidazole derivatives.
2002 Mar
Regulation of a calcium-sensitive K+ channel (cIK1) by protein kinase C.
2002 May 1
Use of intermittent bladder infusion with clotrimazole for treatment of candiduria in a dog.
2002 May 15
Inhibition of vascular smooth muscle cell migration by cytochrome p450 epoxygenase-derived eicosanoids.
2002 May 17
Involvement of nitric oxide and potassium channels in the bradykinin-induced vasodilatation in the rat kidney perfused ex situ.
2002 May 30
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018052Orig1s032lbl.pdf
Vaginal 1% cream: insert an applicator full of cream into the vagina at bedtime for 7 days. External 1% cream for vaginal yeast infections: apply to the skin outside the vagina 2 times daily for up to 7 days. Topical 1% cream: apply a thin layer to the affected area twice daily for 2 weeks (tinea pedis) or 1 week (tinea cruris and tinea corporis).
Route of Administration: Topical
In vitro antifungal activity indicated Clotrimazole (MIC 16 and 8 microg/ml) effective against 68 (70%) of Candida SPP.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:58:44 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:44 UTC 2021
Record UNII
G07GZ97H65
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOTRIMAZOLE
EP   GREEN BOOK   HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN   INCI  
Official Name English
CLOTRIMAZOLE [GREEN BOOK]
Common Name English
SVT-15652
Code English
CLOTRIMAZOLE [WHO-DD]
Common Name English
CLOTRIMAZOLE [USP]
Common Name English
CLOTRIMAZOLE [ORANGE BOOK]
Common Name English
GNF-PF-3499
Code English
TRIVAGIZOLE
Brand Name English
CLOTRIMAZOLE [INN]
Common Name English
CLOTRIMAZOLE [MART.]
Common Name English
CLOTRIMAZOLE [JAN]
Common Name English
CLOTRIMAZOLE COMPONENT OF LOTRISONE
Common Name English
GYNIX
Brand Name English
BAY-5097
Code English
LOTRIMIN
Brand Name English
LOTRISONE COMPONENT CLOTRIMAZOLE
Common Name English
CLOTRIMAZOLE [MI]
Common Name English
GYNE-LOTRIMIN
Brand Name English
BAY 5097
Code English
1-(2-CHLOROTRITYL)IMIDAZOLE
Systematic Name English
CLOTRIMAZOLE [USP MONOGRAPH]
Common Name English
CLOTRIMAZOLE [EP]
Common Name English
MYCELEX
Brand Name English
CLOTRIMAZOLE [EP MONOGRAPH]
Common Name English
NSC-257473
Code English
1-(O-CHLORO-.ALPHA.,.ALPHA.-DIPHENYLBENZYL)IMIDAZOLE
Common Name English
CLOTRIMAZOLE [VANDF]
Common Name English
1-((2-CHLOROPHENYL)DIPHENYLMETHYL)-1H-IMIDAZOLE
Systematic Name English
CLOTRIMAZOLE [USAN]
Common Name English
1H-IMIDAZOLE, 1-((2-CHLOROPHENYL)DIPHENYLMETHYL)-
Systematic Name English
CLOTRIMAZOLE [USP-RS]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.1044G
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
FDA ORPHAN DRUG 204005
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-VATC QJ02AB90
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-VATC QG01AF02
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
NDF-RT N0000008217
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.3
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
CFR 21 CFR 524.450
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
FDA ORPHAN DRUG 216705
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-VATC QA01AB18
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
FDA ORPHAN DRUG 88094
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-VATC QD01AC01
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
LIVERTOX 228
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-ATC D01AC01
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
NDF-RT N0000175487
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-ATC G01AF02
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
NCI_THESAURUS C514
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
WHO-ATC A01AB18
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
CFR 21 CFR 333.210
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
CFR 21 CFR 524.1044H
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
FDA ORPHAN DRUG 520516
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
Code System Code Type Description
MESH
D003022
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
IUPHAR
2330
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
USP_CATALOG
1141002
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
CLOTRIMAZOLE
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-764-8
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
INN
2912
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
MERCK INDEX
M3671
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY Merck Index
EPA CompTox
23593-75-1
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
EVMPD
SUB06777MIG
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
HSDB
3266
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
RXCUI
2623
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00257
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL104
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
PUBCHEM
2812
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
NCI_THESAURUS
C381
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
CAS
23593-75-1
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
LACTMED
Clotrimazole
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
DRUG CENTRAL
719
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
FDA UNII
G07GZ97H65
Created by admin on Fri Jun 25 20:58:44 UTC 2021 , Edited by admin on Fri Jun 25 20:58:44 UTC 2021
PRIMARY
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TRANSPORTER -> INHIBITOR
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