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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H21ClN2O8
Molecular Weight 476.864
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MECLOCYCLINE

SMILES

[H][C@@]12[C@@H](O)[C@]3([H])C(=C)C4=C(Cl)C=CC(O)=C4C(=O)C3=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@H]2N(C)C

InChI

InChIKey=GGQJXCQBBONZFX-IWVLMIASSA-N
InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26,28-30,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1

HIDE SMILES / InChI

Description

Meclocycline is a tetracycline antibiotic. It is used topically for skin infections treatment. Tetracyclines are broad-spectrum bacteriostatic agents and act by inhibiting protein synthesis by blocking the binding of aminoacyl tRNA (transfer RNA) to the mRNA (messenger RNA) ribosome complex. Meclocycline might increase sensitivity to light when it is used with Aminolevulinic acid.

Originator

Blackwood, R.K.
2
Sources: DOI: 10.1021/ja00907a010
Curator's Comment: https://books.google.ru/books?id=0vXTBwAAQBAJ&pg=PA757&lpg=PA757&dq=Meclocycline+1982&source=bl&ots=6IUep2UBpy&sig=cQZ9OF2ixsk8j9wP_oZtJS_iLt0&hl=ru&sa=X&ved=0ahUKEwie2ZidkILMAhXC2CwKHTAtDlkQ6AEIHjAA#v=onepage&q=Meclocycline%201982&f=false

Approval Year

1980
57
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
MECLAN

Approved Use

Topical treatment of inflammatory acne vulgaris

Launch Date

1981
Doses

Doses

DosePopulationAdverse events​
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1675534
Page: p.177
unhealthy, 12-37
n = 33
Health Status: unhealthy
Condition: Acne vulgaris
Age Group: 12-37
Sex: M+F
Population Size: 33
Sources:
https://pubmed.ncbi.nlm.nih.gov/1675534
Page: p.177
Other AEs: Yellow skin...
Other AEs:
Yellow skin (6%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1675534
Page: p.177
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/6452987
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
https://pubmed.ncbi.nlm.nih.gov/6452987
Other AEs: Contact dermatitis...
Other AEs:
Contact dermatitis
Sources:
https://pubmed.ncbi.nlm.nih.gov/6452987
AEs

AEs

AESignificanceDosePopulation
Yellow skin 6%
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/1675534
Page: p.177
unhealthy, 12-37
n = 33
Health Status: unhealthy
Condition: Acne vulgaris
Age Group: 12-37
Sex: M+F
Population Size: 33
Sources:
https://pubmed.ncbi.nlm.nih.gov/1675534
Page: p.177
Contact dermatitis
1 % 2 times / day multiple, topical
Recommended
Dose: 1 %, 2 times / day
Route: topical
Route: multiple
Dose: 1 %, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/6452987
unhealthy
Health Status: unhealthy
Condition: Acne vulgaris
Sources:
https://pubmed.ncbi.nlm.nih.gov/6452987
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1L27GB
ABI Chem
AC1NR077
ABI Chem
AC1NSE5G
Alfa Chemistry
2013-58-3
https://www.alfa-chemistry.com/cas_2013-58-3.htm
AmicBase - Antimicrobial Activities
4057
BioSynth
J-013043
https://www.biosynth.com/en/products/all-products/products/J-013043.html
ChemMol
44014818
http://www.chemmol.com/chemmol/44014818.html
ChemMol
99047357
http://www.chemmol.com/chemmol/99047357.html
Chemieliva Pharmaceutical Co., Ltd
PBCM1229533
Compound Cloud
54676538
Compound Cloud
54676539
DC Chemicals
DC36400
http://www.dcchemicals.com//product_show-GS-2989.html
Molnova
M15822
MuseChem
R074533
https://www.musechem.com/product/R074533.html
NovoSeek
5282519
NovoSeek
5359674
Smolecule
S534870
http://www.smolecule.com/products/s534870
THE BioTek
bt-274529
https://www.thebiotek.com/product/inhibitors/bt-274529
TargetMol
T0281
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.
PH-0154A
ZINC
ZINC000004149268
http://zinc15.docking.org/substances/ZINC000004149268
eMolecules
295160563
PubMed

PubMed

TitleDatePubMed
Patents

Patents

06683067
2
06893665
2
06946118
2
JP2002511777A
414
JP2003515526A
462
JP2009526755A
447
JP2012500274A
12

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Noticeable improvement may be seen in 4 to 6 weeks. In some patients it may require up to 6 to 8 weeks of treatment before noticeable improvement is seen and up to 8 to 12 weeks before maximum benefit is seen.
Two times a day, morning and evening.
Route of Administration: Topical
In Vitro Use Guide
Unknown
Name Type Language
MECLOCYCLINE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide
Common Name English
MECLOCYCLINE [MART.]
Common Name English
MECLOCYCLINE [USAN]
Common Name English
2-NAPHTHACENECARBOXAMIDE, 7-CHLORO-4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYLENE-1,11-DIOXO-, (4S-(4A,4A.ALPHA.,5A,5A.ALPHA.,12A.ALPHA.))-
Common Name English
meclocycline [INN]
Common Name English
MECLOCYCLINE [MI]
Common Name English
NSC-78502
Code English
Meclocycline [WHO-DD]
Common Name English
GS-2989
Code English
Classification Tree Code System Code
NCI_THESAURUS C1595
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
WHO-ATC D10AF04
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
WHO-VATC QD10AF04
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
Code System Code Type Description
RXCUI
29418
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
3333
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
MESH
C100122
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
INN
1566
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
EVMPD
SUB08677MIG
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
WIKIPEDIA
MECLOCYCLINE
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
FDA UNII
23Q8M2HE6S
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID4048567
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
SMS_ID
100000081776
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
217-938-3
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
NCI_THESAURUS
C61825
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL1237124
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
MERCK INDEX
m7119
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB13092
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
CAS
2013-58-3
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
NSC
78502
Created by admin on Sat Dec 16 17:10:30 GMT 2023 , Edited by admin on Sat Dec 16 17:10:30 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of MECLOCYCLINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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