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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H29N3O8
Molecular Weight 487.5033
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SARECYCLINE

SMILES

CN(C)[C@@]1([H])[C@]2([H])C[C@]3([H])Cc4c(ccc(c4C(=O)C3=C([C@@]2(C(=O)C(=C1O)C(=N)O)O)O)O)CN(C)OC

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 487.5033
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02413346 | https://clinicaltrials.gov/ct2/show/NCT02651012 | https://clinicaltrials.gov/ct2/show/NCT02320149 | https://clinicaltrials.gov/ct2/show/NCT02322866 | https://www.drugbank.ca/drugs/DB12035 |

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%.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SEYSARA

Approved Use

Seysara is specifically indicated for the treatment of inflammatory lesions of non-nodular moderate to severe acne vulgaris in patients 9 years of age and older.

Launch Date

1.53826558E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1210 ng/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1590 ng/mL
60 mg 1 times / day steady-state, oral
dose: 60 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1790 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
2570 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
2620 ng/mL
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1700 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FED
2480 ng/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
3820 ng/mL
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
14000 ng × h/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
20700 ng × h/mL
60 mg 1 times / day steady-state, oral
dose: 60 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
21800 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
32200 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
33800 ng × h/mL
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
31800 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FED
43200 ng × h/mL
150 mg single, oral
dose: 150 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
48200 ng × h/mL
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21.9 h
60 mg 1 times / day steady-state, oral
dose: 60 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
20.7 h
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
20.9 h
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SARECYCLINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1.5 mg/kg 1 times / day steady, oral (mean)
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p.93
unhealthy, 19.7 years (range: 9 to 45 years)
n = 1300
Health Status: unhealthy
Condition: acne vulgaris
Age Group: 19.7 years (range: 9 to 45 years)
Sex: M+F
Population Size: 1300
Sources: Page: p.93
Disc. AE: Acne, Urticaria...
AEs leading to
discontinuation/dose reduction:
Acne (3 patients)
Urticaria (3 patients)
Sources: Page: p.93
150 mg 1 times / day steady, oral
Recommended
Dose: 150 mg, 1 times / day
Route: oral
Route: steady
Dose: 150 mg, 1 times / day
Sources:
unhealthy, > 9 years
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Sources:
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources:
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources:
Other AEs: Nausea, Vulvovaginal mycotic infection...
Other AEs:
Nausea (3.1%)
Vulvovaginal mycotic infection (0.8%)
Vulvovaginal candidiasis (0.6%)
Sources:
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p. 17
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources: Page: p. 17
Other AEs: Headache, Nasopharyngitis...
Other AEs:
Headache (3.1%)
Nasopharyngitis (2.8%)
Upper respiratory tract infection (1.6%)
Blood creatine phosphokinase increased (1.2%)
Diarrhea (1%)
Oropharyngeal pain (1%)
Sources: Page: p. 17
AEs

AEs

AESignificanceDosePopulation
Acne 3 patients
Disc. AE
1.5 mg/kg 1 times / day steady, oral (mean)
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p.93
unhealthy, 19.7 years (range: 9 to 45 years)
n = 1300
Health Status: unhealthy
Condition: acne vulgaris
Age Group: 19.7 years (range: 9 to 45 years)
Sex: M+F
Population Size: 1300
Sources: Page: p.93
Urticaria 3 patients
Disc. AE
1.5 mg/kg 1 times / day steady, oral (mean)
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p.93
unhealthy, 19.7 years (range: 9 to 45 years)
n = 1300
Health Status: unhealthy
Condition: acne vulgaris
Age Group: 19.7 years (range: 9 to 45 years)
Sex: M+F
Population Size: 1300
Sources: Page: p.93
Vulvovaginal candidiasis 0.6%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources:
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources:
Vulvovaginal mycotic infection 0.8%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources:
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources:
Nausea 3.1%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources:
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources:
Diarrhea 1%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p. 17
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources: Page: p. 17
Oropharyngeal pain 1%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p. 17
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources: Page: p. 17
Blood creatine phosphokinase increased 1.2%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p. 17
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources: Page: p. 17
Upper respiratory tract infection 1.6%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p. 17
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources: Page: p. 17
Nasopharyngitis 2.8%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p. 17
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources: Page: p. 17
Headache 3.1%
1.5 mg/kg 1 times / day steady, oral (mean)
Recommended
Dose: 1.5 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 1.5 mg/kg, 1 times / day
Sources: Page: p. 17
unhealthy, > 9 years
n = 1064
Health Status: unhealthy
Condition: acne vulgaris
Age Group: > 9 years
Population Size: 1064
Sources: Page: p. 17
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 6.95 uM]
yes (co-administration study)
Comment: In a drug interaction study conducted in healthy subjects, co-administration of a single dose of 150 mg sarecycline tablet caused a 26% increase in digoxin Cmax,ss while AUC0-tau,ss did not change compared to that when digoxin was dosed alone.
Page: 58.0
Drug as victimTox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

1.5 mg/kg/day dose of oral sarecycline for duration of 12 week study
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:35:11 UTC 2021
Edited
by admin
on Sat Jun 26 05:35:11 UTC 2021
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
SARECYCLINE [MI]
Common 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
Classification Tree Code System Code
NCI_THESAURUS C1595
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
Code System Code Type Description
INN
9743
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
MERCK INDEX
M12090
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
LACTMED
Sarecycline
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
FDA UNII
94O110CX2E
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
RXCUI
2059018
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
DRUG CENTRAL
5298
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
DRUG BANK
DB12035
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
NCI_THESAURUS
C152299
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
CAS
1035654-66-0
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL2364632
Created by admin on Sat Jun 26 05:35:11 UTC 2021 , Edited by admin on Sat Jun 26 05:35:11 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
IC50
EXCRETED UNCHANGED
After a single oral dose of radiolabeled sarecycline 100 mg, the average recovery of the dose was 42.6% in feces (14.9% as unchanged) and 44.1% in urine (24.7% as unchanged).
FECAL; URINE
BINDER->LIGAND
An in vitro study demonstrated that sarecycline was 62.5% to 74.7% bound to human plasma proteins at tested sarecycline concentrations of 0.5 ?g/mL to 50 ?g/mL.
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

DAILY