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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H29N3O8
Molecular Weight 487.5024
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARECYCLINE

SMILES

CON(C)CC1=CC=C(O)C2=C1C[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C2=O

InChI

InChIKey=PQJQFLNBMSCUSH-SBAJWEJLSA-N
InChI=1S/C24H29N3O8/c1-26(2)18-13-8-11-7-12-10(9-27(3)35-4)5-6-14(28)16(12)19(29)15(11)21(31)24(13,34)22(32)17(20(18)30)23(25)33/h5-6,11,13,18,28,30-31,34H,7-9H2,1-4H3,(H2,25,33)/t11-,13-,18-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H29N3O8
Molecular Weight 487.5024
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Sarecycline (SC1401, WC3035) is a novel, once-daily, tetracycline-derived compound being developed by Paratek Pharmaceuticals and Allergan (previously Actavis) for use in the treatment of acne and rosacea. In preclinical studies, Sarecycline possesses favorable anti-inflammatory activity, plus narrow-spectrum antibacterial activity relative to other tetracycline-derived molecules. Sarecycline has been used in Phase III clinical trials studying the treatment of Acne Vulgaris. The primary objective was to evaluate the efficacy and safety of oral Sarecycline 1.5 mg/kg per day compared to placebo in treating inflammatory acne lesions in subjects with moderate to severe acne. Sarecycline was statistically significantly superior to placebo with respect to primary efficacy endpoints. The most common adverse events (>2%) reported in the sarecycline group were nausea (3.2%), nasopharyngitis (2.8%), and headache (2.8%). The rate of discontinuation due to adverse events among sarecycline-treated patients in the two studies combined was 1.4%.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SEYSARA
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
1.5 mg/kg/day dose of oral sarecycline for duration of 12 week study
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Tue Mar 06 15:59:03 UTC 2018
Edited
by admin
on Tue Mar 06 15:59:03 UTC 2018
Record UNII
94O110CX2E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SARECYCLINE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
SARECYCLINE [WHO-DD]
Common Name English
(4S,4AS,5AR,12AS)-4-(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-7-((METHOXYMETHYLAMINO)METHYL)-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDROTETRACENE-2-CARBOXAMIDE
Systematic Name English
(4S,4AS,5AR,12AS)-4-(DIMETHYLAMINO)-3,10,12,12A-TETRAHYDROXY-7-((METHOXY(METHYL)AMINO)METHYL)-1,11-DIOXO-1,4,4A,5,5A,6,11,12AOCTAHYDROTETRACENE-2-CARBOXAMIDE
Systematic Name English
P-005672
Code English
SARECYCLINE [INN]
Common Name English
SARECYCLINE [USAN]
Common Name English
2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,10,12,12A-TETRAHYDROXY-7-((METHOXYMETHYLAMINO)METHYL)-1,11-DIOXO-, (4S,4AS,5AR,12AS)-
Common Name English
Code System Code Type Description
INN
9743
Created by admin on Tue Mar 06 15:59:03 UTC 2018 , Edited by admin on Tue Mar 06 15:59:03 UTC 2018
PRIMARY
CAS
1035654-66-0
Created by admin on Tue Mar 06 15:59:03 UTC 2018 , Edited by admin on Tue Mar 06 15:59:03 UTC 2018
PRIMARY
ChEMBL
CHEMBL2364632
Created by admin on Tue Mar 06 15:59:03 UTC 2018 , Edited by admin on Tue Mar 06 15:59:03 UTC 2018
PRIMARY
Related Record Type Details
ACTIVE MOIETY