Dopamine prodrug
Pharmaceutical compound
Docarpamine Trade names Tanadopa Other names TA-870; TA870; N -(N -Acetyl-L -methionyl)-O ,O -bis(ethoxycarbonyl)dopamine Routes of Oral , intravenous [ 1] Drug class Dopamine prodrug ; Dopamine receptor agonist
[4-[2-[[(2S )-2-acetamido-4-methylsulfanylbutanoyl]amino]ethyl]-2-ethoxycarbonyloxyphenyl] ethyl carbonate
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA ) Formula C 21 H 30 N 2 O 8 S Molar mass −1 3D model (JSmol )
CCOC(=O)OC1=C(C=C(C=C1)CCNC(=O)[C@H](CCSC)NC(=O)C)OC(=O)OCC
InChI=1S/C21H30N2O8S/c1-5-28-20(26)30-17-8-7-15(13-18(17)31-21(27)29-6-2)9-11-22-19(25)16(10-12-32-4)23-14(3)24/h7-8,13,16H,5-6,9-12H2,1-4H3,(H,22,25)(H,23,24)/t16-/m0/s1
Key:ZLVMAMIPILWYHQ-INIZCTEOSA-N
Docarpamine (INN Tooltip International Nonproprietary Name , JAN Tooltip Japanese Accepted Name ), sold under the brand name Tanadopa , is an orally active dopamine prodrug which is marketed in Japan for the treatment of acute cardiac insufficiency and/or chronic heart failure .[ 2] [ 3] [ 4] [ 5] [ 6] intravenously .[ 1]
In terms of bioactivation , the hydroxyl groups of docarpamine are freed by esterases in the gut and liver and the amino group is freed by γ-glutamyltransferase in the kidney and liver.[ 5] [ 1] [ 7] intermediate , dideethoxycarbonyldocarpamine (DECD), in which the hydroxyl substitutions have been hydrolyzed .[ 1] N -substitution protects the drug from first-pass metabolism by monoamine oxidase (MAO) until it is cleaved into dopamine and allows it to be orally active.[ 6] [ 7] blood–brain barrier or affect the central nervous system even at high doses and hence is peripherally selective .[ 1] [ 8] [ 3] log P (XLogP3 ) of docarpamine is 2.9.[ 9] D1 receptors .[ 3]
Although docarpamine is orally active and can achieve therapeutic levels of dopamine in blood,[ 1] mg every 8 hours) are required when it is used by this route.[ 5] [ 4] [ 10] duration of action orally is described as greater than 4 hours.[ 4]
The drug was first described in the scientific literature by 1980.[ 2]
See also
References
^ a b c d e f Tekade RK (2020). The Future of Pharmaceutical Product Development and Research ISBN 978-0-12-814456-5 . Retrieved 13 November 2024 . ^ a b Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 . Retrieved 13 November 2024 . ^ a b c "DOCARPAMINE" . Inxight Drugs . Retrieved 13 November 2024 .^ a b c Better O, Greger R, Busch A, Knauf H, Dorup J, Mutschler E, et al. (2012). Diuretics ISBN 978-3-642-79565-7 . Retrieved 13 November 2024 . ^ a b c Seldin DW, Giebisch GH (1997). Diuretic Agents: Clinical Physiology and Pharmacology ISBN 978-0-08-053046-8 . Retrieved 13 November 2024 . ^ a b Finberg J, Youdim M, Riederer P, Tipton K (2013). MAO - The Mother of all Amine Oxidases ISBN 978-3-7091-6499-0 . Retrieved 13 November 2024 . ^ a b Dhaneshwar SS, Sharma M, Patel V, Desai U, Bhojak J (2011). "Prodrug strategies for antihypertensives". Current Topics in Medicinal Chemistry . 11 (18): 2299– 2317. doi :10.2174/156802611797183285 . PMID 21671866 . ^ Jana S, Mandlekar S, Marathe P (2010). "Prodrug design to improve pharmacokinetic and drug delivery properties: challenges to the discovery scientists". Current Medicinal Chemistry . 17 (32): 3874– 3908. doi :10.2174/092986710793205426 . PMID 20858214 . ^ "Docarpamine" . PubChem . Retrieved 13 November 2024 .^ Brinsden PR (2005). A Textbook of In Vitro Fertilization and Assisted Reproduction: The Bourn Hall Guide to Clinical and Laboratory Practice ISBN 978-1-84214-293-6 . Retrieved 13 November 2024 .
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted
1-Aminomethylindanes (e.g., 2CB-Ind , AMMI , bromojimscaline , jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CJP 2CLisaB 2CLisaH 3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g., 3-phenylpiperidine , 3-PPP , OSU-6162 (PNU-96391) , LPH-5 , LPH-48 , Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g., adrenochrome , adrenolutin )Benzazepines (e.g., fenoldopam , lorcaserin , SCHEMBL5334361 )Benzocyclobutenes (e.g., 2CBCB-NBOMe , bromotomscaline , S33005 , TCB-2 , tomscaline )Benzoxepins (e.g., BBOX , IBOX , TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol DMBMPP Ergolines (e.g., LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g., NDTDI , RU-27849 , DEIMDHPCA , DEMPDHPCA , DEMPDHPCA-2C-D , RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g., DMCPA , TMT , tranylcypromine )Phenylpiracetams (e.g., phenylpiracetam , MRZ-9547 , RGPU-95 )Pyridopyrroloquinoxalines (e.g., lumateperone , deulumateperone , IHCH-7079 , IHCH-7086 , IHCH-7113 , ITI-1549 )Tetrahydrobenzopyranylamines (e.g., CT-5126 )Tolazoline Tricyclics (e.g., AMDA , AMDH , benzoctamine , dizocilpine , SpAMDA )ZC-B
Related compounds
2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g., 1,3-DMBA Tooltip 1,3-dimethylbutylamine , 1,4-DMAA Tooltip 1,4-dimethylamylamine , heptaminol , iproheptine , isometheptene , methylhexanamine/1,3-DMAA , octodrine , oenethyl , tuaminoheptane )Benzylamines (e.g., benzylamine , α-methylbenzylamine , MDM1EA , ALPHA , M-ALPHA , pargyline )Benzylpiperazines (e.g., benzylpiperazine , MDBZP , fipexide )Cyclohexylaminopropanes (e.g., propylhexedrine , norpropylhexedrine )Cyclopentylaminopropanes (e.g., isocyclamine , cyclopentamine )Phenoxyethylamines (e.g., 3,4,5-trimethoxyphenoxyethylamine , CT-4719 , ORG-37684 )Phenylalkenylamines (e.g., phenylbutenamine )Phenylalkynylamines (e.g., phenylbutynamine )Phenylpiperazines (e.g., 1-phenylpiperazine , mCPP Tooltip meta-chlorophenylpiperazine , TFMPP Tooltip trifluoromethylphenylpiperazine , oMPP Tooltip ortho-methylphenylpiperazine , pFPP Tooltip para-fluorophenylpiperazine , pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g., phenylpropylamine , homo-MDA , homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g., thiopropamine , methiopropamine , thiothinone )
