Details of the Drug

General Information of Drug (ID: DMZEPFJ)

Drug Name

Demeclocycline

Synonyms

Bioterciclin; Clortetrin; DMCT; DMCTC; Declomycin; Deganol; Demeclociclina; Demeclocyclinum; Demeclor; Demethylchlorotetracycline; Demethylchlortetracyclin; Demethylchlortetracycline; Demethylchlortetracyclinum; Demetraclin; Diuciclin; Ledermycin; Methylchlorotetracycline; Mexocine; Novotriclina; Perciclina; Sumaclina; Demeclocycline Monohydrochloride; Demethylchlortetracycline base; Ledermycin hydrochloride; RP 10192; DMCT (antibiotic); Declomycin (TN); Declostatin (TN); Demeclociclina [INN-Spanish]; Demeclocycline (USP); Demeclocycline [USAN:BAN]; Demeclocyclinum [INN-Latin]; Demethylchlortetracycline (JAN); Ledermycin (TN); Tri-demethylchlortetracycline; [4S-(4alpha,4aalpha,5aalpha,6beta,12aalpha)]-7-chloro-4-(dimethylamino)1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide; (2E)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (2E,4S,4aS,5aS,6R,12aR)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (2E,4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (2Z,4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; (4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; 2-[amino(hydroxy)methylidene]-7-chloro-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-4a,5,5a,6-tetrahydro-4H-tetracene-1,3,12-trione; 6-Demethyl-7-chlorotetracycline; 6-Demethyl-7-chlortetracycline; 6-Demethylchlorotetracycline; 6-Demethylchlortetracycline; 6-Demetil-7-clorotetraciclina; 6-Demetil-7-clorotetraciclina [Italian]; 7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide; 7-Chloro-4-dimethylamino-3,6,10,12,12a-pentahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide; 7-Chloro-6-demethyltetracycline

Indication

Disease Entry	ICD 11	Status	REF
Acne vulgaris	ED80	Approved	[1]
Actinomycosis	N.A.	Approved	[2]
Acute gonococcal cervicitis	N.A.	Approved	[2]
Bronchitis	CA20	Approved	[1]
Brucellosis	N.A.	Approved	[2]
Chancroid	N.A.	Approved	[2]
Lyme disease	1C1G	Approved	[1]
Lymphogranuloma venereum	N.A.	Approved	[2]
Ornithosis	N.A.	Approved	[2]
Pneumonia	CA40	Approved	[2]
Q fever	N.A.	Approved	[2]
Relapsing fever	N.A.	Approved	[2]
Rickettsialpox	N.A.	Approved	[2]
Rocky mountain spotted fever	N.A.	Approved	[2]
Staphylococcus aureus infection	N.A.	Approved	[2]
Syphilis	N.A.	Approved	[2]
Trachoma	N.A.	Approved	[2]
Typhus	N.A.	Approved	[2]
Urinary tract infection	GC08	Approved	[2]
Yaws	N.A.	Approved	[2]
Sinusitis	CA0A.Z	Investigative	[2]
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Therapeutic Class

Antibiotics

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

464.9

Logarithm of the Partition Coefficient (xlogp)

0.7

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is readily absorbed []
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability: 66% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 1.1 mL/min/kg [5]
Elimination: 47% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 10 - 17 hours [5]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 32.26756 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.59% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.3 L/kg [5]
Water Solubility: The ability of drug to dissolve in water is measured as 1.5 mg/mL [3]

Chemical Identifiers

Formula: C21H21ClN2O8
IUPAC Name: (4S,4aS,5aS,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
Canonical SMILES: CN(C)[C@H]1[C@@H]2C[C@@H]3[C@@H](C4=C(C=CC(=C4C(=C3C(=O)[C@@]2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O
InChI: 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/h3-4,6-7,14-15,25-27,30,32H,5H2,1-2H3,(H2,23,31)/t6-,7-,14-,15-,21-/m0/s1
InChIKey: GUXHBMASAHGULD-SEYHBJAFSA-N

Cross-matching ID

PubChem CID: 54680690
ChEBI ID: CHEBI:4392
CAS Number: 127-33-3
DrugBank ID: DB00618
TTD ID: D0R9WP
ACDINA ID: D00178

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Staphylococcus 30S ribosomal subunit (Stap-coc pbp2)	TTQ8KVI	F4NA87_STAAU	Binder	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Demeclocycline (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Sodium bicarbonate	DMMU6BJ	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Demeclocycline caused by Sodium bicarbonate mediated altered urine pH.	Acidosis [5C73]	[8]
Tromethamine	DMOBLGK	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Demeclocycline caused by Tromethamine mediated altered urine pH.	Acidosis [5C73]	[8]
Tretinoin	DM49DUI	Major	Increased risk of pseudotumor cerebri by the combination of Demeclocycline and Tretinoin.	Acne vulgaris [ED80]	[9]
Isotretinoin	DM4QTBN	Major	Increased risk of pseudotumor cerebri by the combination of Demeclocycline and Isotretinoin.	Acne vulgaris [ED80]	[9]
Magnesium Sulfate	DMVEK07	Moderate	Decreased absorption of Demeclocycline due to formation of complexes caused by Magnesium Sulfate.	Acute pain [MG31]	[10]
Aminophylline	DML2NIB	Moderate	Decreased metabolism of Demeclocycline caused by Aminophylline mediated inhibition of CYP450 enzyme.	Asthma [CA23]	[11]
Mestranol	DMG3F94	Moderate	Decreased absorption of Demeclocycline due to formation of complexes caused by Mestranol.	Contraceptive management [QA21]	[12]
Atracurium	DM42HXN	Moderate	Additive neuromuscular blocking effects by the combination of Demeclocycline and Atracurium.	Corneal disease [9A76-9A78]	[13]
Mivacurium	DM473VD	Moderate	Additive neuromuscular blocking effects by the combination of Demeclocycline and Mivacurium.	Corneal disease [9A76-9A78]	[13]
Pancuronium	DMB0VY8	Moderate	Additive neuromuscular blocking effects by the combination of Demeclocycline and Pancuronium.	Corneal disease [9A76-9A78]	[13]
Oxtriphylline	DMLHSE3	Moderate	Decreased metabolism of Demeclocycline caused by Oxtriphylline mediated inhibition of CYP450 enzyme.	Cough [MD12]	[11]
Mycophenolic acid	DMRBMAU	Moderate	Altered absorption of Demeclocycline due to GI flora changes caused by Mycophenolic acid.	Crohn disease [DD70]	[14]
SODIUM CITRATE	DMHPD2Y	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Demeclocycline caused by SODIUM CITRATE mediated altered urine pH.	Discovery agent [N.A.]	[8]
Digitoxin	DMWVIGP	Moderate	Altered absorption of Demeclocycline due to GI flora changes caused by Digitoxin.	Heart failure [BD10-BD1Z]	[15]
Mipomersen	DMGSRN1	Major	Increased risk of hepatotoxicity by the combination of Demeclocycline and Mipomersen.	Hyper-lipoproteinaemia [5C80]	[16]
BMS-201038	DMQTAGO	Major	Increased risk of hepatotoxicity by the combination of Demeclocycline and BMS-201038.	Hyper-lipoproteinaemia [5C80]	[17]
Quinapril	DMR8H31	Moderate	Decreased absorption of Demeclocycline due to formation of complexes caused by Quinapril.	Hypertension [BA00-BA04]	[18]
Sodium acetate anhydrous	DMH21E0	Moderate	as urine pH determines the ionization state of weakly acidic or weakly alkaline drugs. Demeclocycline caused by Sodium acetate anhydrous mediated altered urine pH.	Hypo-osmolality/hyponatraemia [5C72]	[8]
Iron	DMAP8MV	Moderate	Decreased absorption of Demeclocycline due to formation of complexes caused by Iron.	Iron deficiency anaemia [3A00]	[19]
Porfimer Sodium	DM7ZWNY	Moderate	Increased risk of photosensitivity reactions by the combination of Demeclocycline and Porfimer Sodium.	Lung cancer [2C25]	[20]
Calaspargase pegol	DMQZBXI	Moderate	Increased risk of hepatotoxicity by the combination of Demeclocycline and Calaspargase pegol.	Malignant haematopoietic neoplasm [2B33]	[21]
Idelalisib	DM602WT	Moderate	Increased risk of hepatotoxicity by the combination of Demeclocycline and Idelalisib.	Mature B-cell leukaemia [2A82]	[22]
Ethinyl estradiol	DMODJ40	Moderate	Decreased absorption of Demeclocycline due to formation of complexes caused by Ethinyl estradiol.	Menopausal disorder [GA30]	[12]
Lanthanum carbonate	DMMJQSH	Moderate	Decreased absorption of Demeclocycline due to formation of complexes caused by Lanthanum carbonate.	Mineral absorption/transport disorder [5C64]	[23]
Ranitidine	DM0GUSX	Moderate	Decreased absorption of Demeclocycline due to formation of complexes caused by Ranitidine.	Peptic ulcer [DA61]	[24]
Vecuronium	DMP0UK2	Moderate	Additive neuromuscular blocking effects by the combination of Demeclocycline and Vecuronium.	Tonus and reflex abnormality [MB47]	[13]
Rocuronium	DMY9BMK	Moderate	Additive neuromuscular blocking effects by the combination of Demeclocycline and Rocuronium.	Tonus and reflex abnormality [MB47]	[13]
Mycophenolate mofetil	DMPQAGE	Moderate	Altered absorption of Demeclocycline due to GI flora changes caused by Mycophenolate mofetil.	Transplant rejection [NE84]	[14]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 27	E00381	83511	Colorant
D&C red no. 30	E00456	3000709	Colorant
FD&C blue no. 1	E00263	19700	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sodium stearyl fumarate	E00545	23665634	lubricant
Sunset yellow FCF	E00255	17730	Colorant
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Hexahydric alcohol	E00083	5780	Diluent; Flavoring agent; Humectant; Plasticizing agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Lithol rubin BCA	E00607	135423095	Colorant
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Demeclocycline 150 mg tablet	150 mg	Oral Tablet	Oral
Demeclocycline 300 mg tablet	300 mg	Oral Tablet	Oral

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Demeclocycline FDA Label
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Detection of tetracycline resistance genes by PCR methods. Methods Mol Biol. 2004;268:3-13.
8	Elliott GR "Sodium bicarbonate and oral tetracycline." Clin Pharmacol Ther 13 (1972): 459. [PMID: 5026384]
9	Gardner K, Cox T, Digre KB "Idiopathic intracranial hypertension associated with tetracycline use in fraternal twins: case reports and review." Neurology 45 (1995): 6-10. [PMID: 7824136]
10	Covington TR, Lawson LC, Young LL, eds. "Handbook of Nonprescription Drugs. 10th ed." Washington, DC: American Pharmaceutical Association (1993):.
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12	Friedman CI, Huneke AL, Kim MH, Powell J "The effect of ampicillin on oral contraceptive effectiveness." Obstet Gynecol 55 (1980): 33-7. [PMID: 7188714]
13	Multum Information Services, Inc. Expert Review Panel.
14	Product Information. CellCept (mycophenolate mofetil). Roche Laboratories, Nutley, NJ.
15	Lindenbaum J, Rund DG, Butler VP Jr, Tse-Eng D, Saha JR "Inactivation of digoxin by the gut flora: reversal by antibiotic therapy." N Engl J Med 305 (1981): 789-94. [PMID: 7266632]
16	Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
17	Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
18	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
19	Campbell NR, Hasinoff BB "Iron supplements: a common cause of drug interactions." Br J Clin Pharmacol 31 (1991): 251-5. [PMID: 2054263]
20	Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]
21	Al-Nawakil C, Willems L, Mauprivez C, et.al "Successful treatment of l-asparaginase-induced severe acute hepatotoxicity using mitochondrial cofactors." Leuk Lymphoma 55 (2014): 1670-4. [PMID: 24090500]
22	Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
23	Canadian Pharmacists Association.
24	Albert KS, Welch RD, DeSante KA, DiSanto AR "Decreased tetracycline bioavailability caused by a bismuth subsalicylate antidiarrheal mixture." J Pharm Sci 68 (1979): 586-8. [PMID: 435335]