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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H21ClN2O8
Molecular Weight 464.853
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEMECLOCYCLINE

SMILES

CN(C)[C@H]1[C@@H]2C[C@@H]3[C@H](O)C4=C(C(O)=CC=C4Cl)C(=O)C3=C(O)[C@]2(O)C(=O)C(C(N)=O)=C1O

InChI

InChIKey=FMTDIUIBLCQGJB-SEYHBJAFSA-N
InChI=1S/C21H21ClN2O8/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1

HIDE SMILES / InChI

Description

Demeclocycline hydrochloride is an antibiotic isolated from a mutant strain of Streptomyces aureofaciens. It inhibits protein synthesis by binding with the 30S and possibly the 50S ribosomal subunit(s) of susceptible bacteria. Demeclocycline has antimicrobial activity against a wide range of gram-negative and gram-positive organisms. Demeclocycline is indicated in the treatment of infections caused by susceptible strains of the designated microorganisms. Demeclocycline is currently used to treat hyponatremia in patients with the syndrome of inappropriate antidiuretic hormone secretion (SIADH). Demeclocycline mainly attenuates hyponatremia in SIADH by reducing adenylate cyclase 5/6 expression and, consequently, cAMP generation, AQP2 gene transcription, and AQP2 abundance in the renal inner medulla, coinciding with a reduced vasopressin escape response in other collecting duct segments.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Nephrogenic diabetes insipidus induced by demethylchlortetracycline (Declomycin).
1967 Nov
Methacycline and demeclocycline in relation to sunlight.
1971 Apr 12
Demeclocycline-induced renal failure.
1977 Jan 1
Plasma demeclocycline levels and nephrotoxicity. Correlation in hyponatremic cirrhotic patients.
1980 Jun 27
Effect of prostaglandin inhibition on demeclocycline administration in conscious rats.
1980 Sep
[Organic renal insufficiency during treatment with demethylchlortetracycline].
1981 Jan 17
Serious hyponatremia in patients with cancer: management with demeclocycline.
1981 Jun 15
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.
1981 Sep-Oct
Demeclocycline-induced phosphate diabetes in a patient with inappropriate ADH secretion and systemic sarcoidosis.
1993
Syndrome of inappropriate antidiuretic hormone associated with vinorelbine therapy.
1998 Dec
Patents

Sample Use Guides

In Vivo Use Guide
Therapy should be continued for at least 24 to 48 hours after symptoms and fever have subsided. Concomitant therapy: Absorption of tetracyclines is impaired by antacids containing aluminum, calcium, or magnesium, and by iron-containing preparations. Foods and some dairy products also interfere with absorption. Oral forms of tetracycline should be given at least 1 hour before or 2 hours after meals. In patients with renal impairment: Tetracyclines should be used cautiously in patients with impaired renal function. Total dosage should be decreased by reduction of recommended individual doses and/or by extending time intervals between doses. In patients with liver impairment: Tetracyclines should be used cautiously in patients with impaired liver function. Total dosage should be decreased by reduction of recommended individual doses and/or by extending time intervals between doses. Administration of adequate amounts of fluid with the oral formulations of tetracyclines is recommended to wash down the drugs and reduce the risk of esophageal irritation and ulceration. Adults: Usual daily dose – Four divided doses of 150 mg each or two divided doses of 300 mg each. For pediatric patients above eight years of age: Usual daily dose, 7 to 13 mg per kg body weight per day, depending upon the severity of the disease, divided into two to four doses not to exceed adult dosage of 600 mg per day. Gonorrhea patients sensitive to penicillin may be treated with demeclocycline administered as an initial oral dose of 600 mg followed by 300 mg every 12 hours for four days to a total of 3 grams.
Route of Administration: Oral
In Vitro Use Guide
Demeclocycline protects cultured cerebellar granule neurons against glutamate toxicity at doses ranging between 80 and 150 μM.
Name Type Language
DEMECLOCYCLINE
HSDB   INN   MART.   MI   USP   VANDF   WHO-DD  
INN  
Official Name English
CHLORTETRACYCLINE HYDROCHLORIDE IMPURITY B [EP]
Common Name English
DEMECLOCYCLINE [USP]
Common Name English
DEMETHYLCHLORTETRACYCLINE
Common Name English
DEMECLOCYCLINE [MART.]
Common Name English
2-NAPHTHACENECARBOXAMIDE, 7-CHLORO-4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,6,10,12,12A-PENTAHYDROXY-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5A.ALPHA.,6.BETA.,12A.ALPHA.))-
Common Name English
DEMECLOCYCLINE [MI]
Common Name English
7-CHLORO-4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,6,10,12,12A-PENTAHYDROXY-1,11-DIOXO-2-NAPHTHACENECARBOXAMIDE
Common Name English
DEMETHYLCHLORTETRACYCLINE [JAN]
Common Name English
DEMECLOCYCLINE [HSDB]
Common Name English
DEMECLOCYCLINE [VANDF]
Common Name English
DEMECLOCYCLINE [INN]
Common Name English
CHLORTETRACYCLINE HYDROCHLORIDE SPECIFIED IMPURITY B [EP]
Common Name English
DEMECLOCYCLINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01AA01
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
NDF-RT N0000007948
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
WHO-VATC QD06AA01
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
NDF-RT N0000175505
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
NCI_THESAURUS C1595
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
NDF-RT N0000007948
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
WHO-ATC J01AA01
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
WHO-ATC D06AA01
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
LIVERTOX 278
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1591
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
RXCUI
3154
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY RxNorm
ECHA (EC/EINECS)
204-834-8
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
LactMed
127-33-3
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
CAS
127-33-3
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
NCI_THESAURUS
C47980
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
DRUG BANK
DB00618
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
EPA CompTox
127-33-3
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
MERCK INDEX
M4160
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY Merck Index
HSDB
127-33-3
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
INN
917
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
WIKIPEDIA
DEMECLOCYCLINE
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
EVMPD
SUB06963MIG
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY
MESH
D003707
Created by admin on Mon Oct 21 19:49:38 UTC 2019 , Edited by admin on Mon Oct 21 19:49:38 UTC 2019
PRIMARY