Danitracen

Danitracen
Identifiers
	IUPAC name 4-(6H-benzo[c][1]benzothiepin-11-ylidene)-1-methylpiperidine;
CAS Number	1447-70-7;
PubChem CID	35758;
UNII	SD507F5T2W;
ChEMBL	ChEMBL440557;
CompTox Dashboard (EPA)	DTXSID70185156 ;
Chemical and physical data
Formula	C20H21NO
Molar mass	291.394 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC(=C2C3=CC=CC=C3C(C4=CC=CC=C42)O)CC1;
	InChI InChI=1S/C20H21NO/c1-21-12-10-14(11-13-21)19-15-6-2-4-8-17(15)20(22)18-9-5-3-7-16(18)19/h2-9,20,22H,10-13H2,1H3; Key:HLBRHTFSMMEHPK-UHFFFAOYSA-N;

Danitracen (WA 335) is an antidepressant compound developed in the 1970s. Danitracen acts by blocking central and peripheral 5-HT receptors: it potentiates testosterone-induced sexual behavior in rats and abolishes the 5-hydroxytryptophan (5-HTP) induced hypermotility in mice. In amphetamine-treated rats, administration of danitracen lowered whole brain serotonin and norepinephrine levels. Danitracen was investigated in clinical trials in depressed patients. At 3 mg/day, danitracen was equipotent to 150 mg/day amitriptyline.^[1]^[2]^[3]^[4]^[5]^[6]

References

^ Engelhardt G (November 1975). "[On the pharmacology of 9,10-dihydro-10-(1-methyl-4-piperidylidene)-9-anthrol (WA 335), a histamine and serotonin antagonist (author's transl)]". Arzneimittel-Forschung (in German). 25 (11): 1723–37. PMID 1049.
^ "Danitracen". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS).
^ Castañer J, Chatterjee SS (1976). "Danitracen". Drugs of the Future. 1 (6)): 279. doi:10.1358/dof.1976.001.06.1002525.
^ Maj J, Baran L, Sowińska H, Gancarczyk L (1976). "The action of compound WA-335 on the central nervous system". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 205–22. PMID 945051.
^ Maj J, Sowińska H, Baran L (1976). "Influence of WA-335, a factor which blocks serotonin receptors, on neuroleptic-induced catalepsy". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 197–203. PMID 945050.
^ Matussek N, Benkert O, Fidetzis K, Flach D, Hermann HU, Kaumeier S, et al. (1976). "[Comparison of the effects of the anthracene derivative danitracen (WA335-BS) and amitriptyline in depressive patients (author's transl)]". Arzneimittel-Forschung (in German). 26 (6): 1160–2. PMID 786311.

Attribution: some content on this page was copied from the public domain source https://drugs.ncats.io/drug/SD507F5T2W.

[pmid1049-1] Engelhardt G (November 1975). "[On the pharmacology of 9,10-dihydro-10-(1-methyl-4-piperidylidene)-9-anthrol (WA 335), a histamine and serotonin antagonist (author's transl)]". Arzneimittel-Forschung (in German). 25 (11): 1723–37. PMID 1049.

[2] "Danitracen". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS).

[3] Castañer J, Chatterjee SS (1976). "Danitracen". Drugs of the Future. 1 (6)): 279. doi:10.1358/dof.1976.001.06.1002525.

[pmid945051-4] Maj J, Baran L, Sowińska H, Gancarczyk L (1976). "The action of compound WA-335 on the central nervous system". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 205–22. PMID 945051.

[pmid945050-5] Maj J, Sowińska H, Baran L (1976). "Influence of WA-335, a factor which blocks serotonin receptors, on neuroleptic-induced catalepsy". Archivum Immunologiae et Therapiae Experimentalis. 24 (2): 197–203. PMID 945050.

[pmid786311-6] Matussek N, Benkert O, Fidetzis K, Flach D, Hermann HU, Kaumeier S, et al. (1976). "[Comparison of the effects of the anthracene derivative danitracen (WA335-BS) and amitriptyline in depressive patients (author's transl)]". Arzneimittel-Forschung (in German). 26 (6): 1160–2. PMID 786311.

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[2]

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[6]

v t e Tetracyclics
Classes	Polyketides Tetracenes Steroids
Antibiotics	Tetracyclines Tetracycline Chlortetracycline Demeclocycline Doxycycline Eravacycline Lymecycline Minocycline Omadacycline Oxytetracycline Rolitetracycline Sarecycline Glycylcyclines Tigecycline Triterpenes Fusidanes Fusidic acid Helvolic acid Cephalosporin P₁
Antidepressants (TeCAs)	Azipramine Ciclopramine Esmirtazapine Mianserin Mirtazapine Naranol Oxaprotiline Setiptiline
Steroids	Gonanes Steranes Cholane Cholestane Ergostane Sex hormone steroids Androstanes Androstenediol Dehydroepiandrosterone Testosterone Estranes Estetrol Estradiol Estriol Estrone Pregnanes Progestogens Progesterone Progestins Acetomepregenol Chlormadinone acetate Danazol Delmadinone acetate Etonogestrel Gestodene Hydroxyprogesterone caproate Levonorgestrel Norethisterone Norgestrel Segesterone acetate Tibolone Corticosteroids Cortisone Cortisol Prednisone Prednisolone Aldosterone Allopregnanes Norpregnane Retropregnane Sterols Phytosterols Campesterol beta-Sitosterol Ergosterols Secosteroids Ergocalciferol Cholecalciferol Cholesterol Stanol esters Triterpenes Cycloartane Cucurbitacins Cucurbitane Dammarane Euphane Lanostane Protostane

See also

References