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version 2.7.1
Substance Class Chemical
Record UNII
DR5S136IVO
Record Status Validated
Record Version
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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H26ClN7O3
Molecular Weight 483.951
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0
Created by admin on Wed Aug 04 07:13:23 EDT 2021
Edited by admin on Wed Aug 04 07:13:23 EDT 2021
Structure of AVANAFIL

Systematic Names:

  • None recorded

SMILES

COC1=CC=C(CNC2=C(C=NC(=N2)N3CCC[C@H]3CO)C(=O)NCC4=NC=CC=N4)C=C1Cl

InChI

WEAJZXNPAWBCOA-INIZCTEOSA-N
InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
Name Type Language Details Access References
AVANAFIL
Domain Jurisdiction Naming Organization
drug  
INN   USAN  
DASH   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
Official Name
English  
TA-1790
Code
English  
STENDRA
Brand Name
English  
SPEDRA
Brand Name
English  
AVANAFIL [WHO-DD]
Common Name
English  
AVANAFIL [VANDF]
Common Name
English  
AVANAFIL [USAN]
Common Name
English  
AVANAFIL [ORANGE BOOK]
Common Name
English  
AVANAFIL [MI]
Common Name
English  
AVANAFIL [MART.]
Common Name
English  
AVANAFIL [INN]
Common Name
English  
5-PYRIMIDINECARBOXAMIDE, 4-(((3-CHLORO-4-METHOXYPHENYL)METHYL)AMINO)-2-((2S)-2-(HYDROXYMETHYL)-1-PYRROLIDINYL)-N-(2-PYRIMIDINYLMETHYL)-
Systematic Name
English  
4-((3-CHLORO-4-METHOXYBENZYL)AMINO)-2-((2S)-2-(HYDROXYMETHYL)PYRROLIDIN-1-YL)-N-(PYRIMIDIN-2-YLMETHYL)PYRIMIDINE-5-CARBOXAMIDE
Systematic Name
English  
(S)-4-(3-CHLORO-4-METHOXYBENZYLAMINO)-2-(2-HYDROXYMETHYLPYRROLIDIN-1-YL)-N-PYRIMIDIN-2-YLMETHYL-5-PYRIMIDINECARBOXAMIDE
Systematic Name
English  
Classification Tree Code System Code Access References
WHO-ATC G04BE10
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
EMA ASSESSMENT REPORTS SPEDRA (AUTHORIZED: ERECTILE DYSFUNCTIONS)
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
LIVERTOX 78
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
NCI_THESAURUS C2127
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
NDF-RT N0000175599
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
Code System Code Type Description Access References
CAS
330784-47-9
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
EVMPD
SUB34916
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
ChEMBL
CHEMBL1963681
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
DRUG BANK
DB06237
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
DRUG CENTRAL
4305
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
EPA CompTox
330784-47-9
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
FDA UNII
DR5S136IVO
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
INN
8572
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
IUPHAR
7448
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
MERCK INDEX
M2145
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY Merck Index
MESH
C553414
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
NCI_THESAURUS
C74354
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
PUBCHEM
9869929
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
RXCUI
1291301
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY RxNorm
WIKIPEDIA
Avanafil
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
PRIMARY
Related Record Type Details Access References
EXCRETED UNCHANGED
Mediator Substance Details
none
FECAL
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
OFF-TARGET->INHIBITOR
Mediator Substance Details
none
Avanafil inhibited hERG current in a concentration-dependent manner with IC50 of 15.8 ?M, which corresponded to exposures approximately 290-fold above the unbound Cmax (~26 ng/mL, 0.054 ?M) in human subjects after the maximum recommended single oral dose at 200 mg.
IC50
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
BINDER->LIGAND
Mediator Substance Details
none
BINDING
Created by admin on Wed Aug 04 07:13:26 EDT 2021 , Edited by admin on Wed Aug 04 07:13:26 EDT 2021
METABOLIC ENZYME -> SUBSTRATE
Mediator Substance Details
none
MAJOR
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
Related Record Type Details Access References
METABOLITE -> PARENT
Mediator Substance Details
none
FECAL; PLASMA; URINE
Created by admin on Wed Aug 04 07:13:36 EDT 2021 , Edited by admin on Wed Aug 04 07:13:36 EDT 2021
METABOLITE -> PARENT
Mediator Substance Details
none
PLASMA
Created by admin on Wed Aug 04 07:13:36 EDT 2021 , Edited by admin on Wed Aug 04 07:13:36 EDT 2021
METABOLITE INACTIVE -> PARENT
Mediator Substance Details
none
MAJOR
FECAL; PLASMA; URINE
Created by admin on Wed Aug 04 07:13:36 EDT 2021 , Edited by admin on Wed Aug 04 07:13:36 EDT 2021
METABOLITE -> PARENT
Mediator Substance Details
none
PLASMA
Created by admin on Wed Aug 04 07:13:36 EDT 2021 , Edited by admin on Wed Aug 04 07:13:36 EDT 2021
METABOLITE -> PARENT
none
Mediator Substance Details
none
Created by admin on Wed Aug 04 07:13:23 EDT 2021 , Edited by admin on Wed Aug 04 07:13:23 EDT 2021
Related Record Type Details Access References
ACTIVE MOIETY
none
none
Mediator Substance Details
none
Created by admin on Wed Aug 04 07:13:36 EDT 2021 , Edited by admin on Wed Aug 04 07:13:36 EDT 2021
Name Property Type Amount Referenced Substance Defining Parameters Access References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC
Tmax PHARMACOKINETIC if Avanafil is taken with a high fat meal

Note Access References
[Validation]WARNING:Code 'N0000175599'[NDF-RT] collides (possible duplicate) with existing code & codeSystem for substance:
[742SXX0ICT]TADALAFIL
Created Wed Aug 04 07:13:23 EDT 2021
Created By admin
Last Edited Wed Aug 04 07:13:23 EDT 2021
Last Edited By admin
Index Source Text / Citation Source Type Tags Date Accessed File Access
1 GSRS System-generated Validation messages VALIDATION_MESSAGE Wed Aug 04 07:13:22 EDT 2021
2 http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/002581/human_med_001661. SRS NOMEN
3 SRS import [DR5S136IVO] SRS NOMEN Fri Apr 28 14:42:37 EDT 2017
4 http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm302140.htm SRS NOMEN
5 http://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf WEBSITE NOMEN
6 INN Proposed List 92 INN_LIST PUBLIC_DOMAIN_RELEASE
7 ORANGE BOOK SRS NOMEN
8 MARTINDALE 2011 SRS NOMEN
9 USP Dictionary 2010 SRS NOMEN PUBLIC_DOMAIN_RELEASE AUTO_SELECTED
10 AVANAFIL [DASH] SRS_LOCATOR
11 AVANAFIL [USAN] SRS_LOCATOR
12 NDF-RT SRS NOMEN
13 USP DICTIONARY 2011 SRS NOMEN
14 AVANAFIL [MART.] SRS_LOCATOR
15 WHO-DD SRS NOMEN
16 SYSTEM
17 http://fco.factsandcomparisons.com/lco/action/doc/retrieve/docid/fc_dfc/5548926#f_pharmacokinetics LEPINDEX
18 USP DICTIONARY 2010 SRS NOMEN
19 https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf NDA PUBLIC REVIEW PUBLIC_DOMAIN_RELEASE
20 STN STN (SCIFINDER)
21 https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf NDA PUBLIC REVIEW PUBLIC_DOMAIN_RELEASE
22 AVANAFIL [INN] SRS_LOCATOR
23 dump-public-2021-07-22_UPDATED.gsrs BATCH_IMPORT Wed Aug 04 07:13:21 EDT 2021
24 SRS CODE IMPORT SRS NOMEN Fri Apr 28 14:42:37 EDT 2017
25 https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202276s000lbl.pdf NDA PUBLIC REVIEW PUBLIC_DOMAIN_RELEASE
26 WIKI WIKI NOMEN PUBLIC_DOMAIN_RELEASE
27 AVANAFIL [VANDF] SRS_LOCATOR
28 AVANAFIL [ORANGE BOOK] SRS_LOCATOR
29 USAN COUN 2004 USANCOUN NOMEN PUBLIC_DOMAIN_RELEASE
30 WEBSITE WEBSITE NOMEN PUBLIC_DOMAIN_RELEASE
31 https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000PharmR.pdf NDA PUBLIC REVIEW PUBLIC_DOMAIN_RELEASE
32 https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202276Orig1s000ClinPharmR.pdf NDA PUBLIC REVIEW PUBLIC_DOMAIN_RELEASE
33 AVANAFIL [MI] SRS_LOCATOR
34 WEB PAGE WEB PAGE NOMEN
35 AVANAFIL [WHO-DD] SRS_LOCATOR
36 MERCK SRS NOMEN

Molecular Formula C23H26ClN7O3
Molecular Weight 483.951
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED