demeclocycline ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antibiotics, protein-synthesis inhibitors, tetracycline derivatives 802 127-33-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • demeclocycline
  • demethylchlortetracycline
  • demeclocycline hydrochloride
  • demeclocycline HCl
The tetracyclines are primarily bacteriostatic and are thought to exert their antimicrobial effect by the inhibition of protein synthesis. The tetracyclines, including demeclocycline have a similar antimicrobial spectrum of activity against a wide range of gram-negative and gram-positive organisms.
  • Molecular weight: 464.86
  • Formula: C21H21ClN2O8
  • CLOGP: -1.01
  • LIPINSKI: 1
  • HAC: 10
  • HDO: 6
  • TPSA: 181.62
  • ALOGS: -2.94
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.60 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1.50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 47 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 32.27 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 66 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.10 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.59 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 12 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 14, 1960 FDA LEDERLE

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Paraneoplastic rash 50.89 47.72 6 336 81 64498309
Diabetes insipidus 50.51 47.72 10 332 4511 64493879

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D06AA01 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
ANTIBIOTICS FOR TOPICAL USE
Tetracycline and derivatives
ATC J01AA01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
TETRACYCLINES
Tetracyclines
FDA CS M0021223 Tetracyclines
FDA EPC N0000175505 Tetracycline-class Antimicrobial
CHEBI has role CHEBI:36047 antibacterial drugs
CHEBI has role CHEBI:176497 geroprotectors
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000890 Anti-Infective Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Trachoma indication 2576002 DOID:11265
Actinomycotic infection indication 11817007 DOID:8478
Gonorrhea indication 15628003 DOID:7551
Infection of skin AND/OR subcutaneous tissue indication 19824006
Gingivostomatitis indication 20607006
Acute gonococcal cervicitis indication 20943002 DOID:10615
Granuloma inguinale indication 28867007 DOID:9113
Acute gonococcal urethritis indication 29864006
Bronchitis indication 32398004 DOID:6132
Sinusitis indication 36971009
Gonorrhea of rectum indication 42746002
Klebsiella cystitis indication 60867007
Acute gonococcal endometritis indication 65295003 DOID:7527
Urinary tract infectious disease indication 68566005
Yaws indication 70647001 DOID:10371
Gonorrhea of pharynx indication 74372003
Rickettsialpox indication 75096007 DOID:11103
Ornithosis indication 75116005 DOID:11262
Acute bacterial sinusitis indication 75498004
Brucellosis indication 75702008 DOID:11077
Syphilis indication 76272004
Rocky Mountain spotted fever indication 186772009
Q fever indication 186788009 DOID:11100
Lymphogranuloma venereum indication 186946009 DOID:13819
Pneumonia indication 233604007 DOID:552
Inclusion conjunctivitis indication 266109000
Chancroid indication 266143009 DOID:13778
Infective otitis media indication 312218008
Pharyngitis indication 405737000 DOID:2275
Infection due to Staphylococcus aureus indication 406602003
Anthrax indication 409498004 DOID:7427
Relapsing fever indication 420079008 DOID:13034
Haemophilus Influenzae Pharyngitis indication
Typhus Infections indication
Haemophilus Influenzae Acute Otitis Media indication
Tularemia off-label use 19265001
Enterocolitis off-label use 43752006
Pneumonia due to Mycoplasma pneumoniae off-label use 46970008
Syndrome of inappropriate vasopressin secretion off-label use 55004003 DOID:3401
Plague off-label use 58750007 DOID:3482
Cholangitis off-label use 82403002 DOID:9446
Chlamydial infection off-label use 105629000
Infectious disease of abdomen off-label use 128070006
Ocular rosacea off-label use 200933006
Diabetes insipidus contraindication 15771004 DOID:9409
Kidney disease contraindication 90708001 DOID:557
Pregnancy, function contraindication 289908002
Pseudomembranous enterocolitis contraindication 397683000
Breastfeeding (mother) contraindication 413712001




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.25 acidic
pKa2 7.09 acidic
pKa3 7.7 acidic
pKa4 11.73 acidic
pKa5 12.35 acidic
pKa6 13.08 acidic
pKa7 9.5 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Estrogen receptor beta Nuclear hormone receptor IC50 7.21 CHEMBL
30S ribosomal protein S4 Ribosomal protein WOMBAT-PK
30S ribosomal protein S9 Ribosomal protein WOMBAT-PK

External reference:

IDSource
4019707 VUID
N0000147799 NUI
D03680 KEGG_DRUG
64-73-3 SECONDARY_CAS_RN
3154 RXNORM
4017921 VANDF
4019707 VANDF
C0011276 UMLSCUI
CHEBI:4392 CHEBI
CHEMBL1591 ChEMBL_ID
CHEMBL1200474 ChEMBL_ID
D003707 MESH_DESCRIPTOR_UI
DB00618 DRUGBANK_ID
10905 IUPHAR_LIGAND_ID
917 INN_ID
5R5W9ICI6O UNII
54680690 PUBCHEM_CID
4543 MMSL
50744 MMSL
d01068 MMSL
002745 NDDF
004862 NDDF
10324005 SNOMEDCT_US
372779007 SNOMEDCT_US
5737008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-625 TABLET, FILM COATED 150 mg ORAL ANDA 25 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-626 TABLET, FILM COATED 300 mg ORAL ANDA 25 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24658-710 TABLET, FILM COATED 150 mg ORAL ANDA 21 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 24658-711 TABLET, FILM COATED 300 mg ORAL ANDA 21 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-143 TABLET, FILM COATED 150 mg ORAL ANDA 21 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-144 TABLET, FILM COATED 300 mg ORAL ANDA 21 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53746-554 TABLET 150 mg ORAL ANDA 13 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53746-555 TABLET 300 mg ORAL ANDA 13 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-649 TABLET, FILM COATED 300 mg ORAL ANDA 21 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 60429-663 TABLET, FILM COATED 150 mg ORAL ANDA 21 sections
demeclocycline hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 61748-113 TABLET, FILM COATED 300 mg ORAL ANDA 27 sections
demeclocycline hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 61748-115 TABLET, FILM COATED 150 mg ORAL ANDA 27 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 62584-159 TABLET 150 mg ORAL ANDA 24 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 62584-163 TABLET 300 mg ORAL ANDA 24 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-554 TABLET 150 mg ORAL ANDA 13 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 65162-555 TABLET 300 mg ORAL ANDA 13 sections
Demeclocycline Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 68151-0155 TABLET 150 mg ORAL ANDA 12 sections