Details of the Drug

General Information of Drug (ID: DMSLJP4)

Drug Name

Ziconotide

Synonyms

Prialt; Ziconotide [USAN]; SNX 111; DRG-0250; Omega-Conotoxin M VIIA; Omega-conotoxin MVIIA; Prialt (TN); SNX-111; Omega-ConopeptideMVIIA (Conus); Omega-Conotoxin mviia, conus magus; Omega-Conotoxin M VIIA (reduced), cyclic (1-16),(8-20),(15-25)-tris(disulfide)

Indication

Disease Entry	ICD 11	Status	REF
Pain	MG30-MG3Z	Approved	[1]
Traumatic brain injury	NA07.Z	Phase 1/2	[1]
Chronic pain	MG30	Investigative	[2]

Therapeutic Class

Analgesics

Affected Organisms

Humans and other mammals

ATC Code

N02BG08: Ziconotide

N02BG: Other analgesics and antipyretics

N02B: OTHER ANALGESICS AND ANTIPYRETICS

N02: ANALGESICS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

2639.2

Logarithm of the Partition Coefficient (xlogp)

-14

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption AUC: The area under the plot of plasma concentration (AUC) of drug is 83.6-608 mcgh/L [3]
Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 16.4-132 mcg/L [3]
Clearance: The clearance of drug is 0.38 +/- 0.56 mL/min [3]
Elimination: less than 1% of drug is recovered in urine [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 3.7 - 5.5 hours [3]
Metabolism: The drug is metabolized via various peptidases upon entering systemic circulation [3]
Unbound Fraction: The unbound fraction of drug in plasma is 0.5% [4]
Vd: The volume of distribution (Vd) of drug is 0.155 +/- 0.263 L [3]

Chemical Identifiers

Formula: C102H172N36O32S7
IUPAC Name: 2-[(1R,4S,7S,13S,16R,21R,24S,27S,30S,33S,36S,39S,42R,45S,48S,54S,60S,63R,68R,71S,77S)-63-amino-13,45,54,60-tetrakis(4-aminobutyl)-4,36-bis(3-carbamimidamidopropyl)-16-carbamoyl-71-[(1R)-1-hydroxyethyl]-7,39,77-tris(hydroxymethyl)-27-[(4-hydroxyphenyl)methyl]-48-methyl-33-(2-methylpropyl)-30-(2-methylsulfanylethyl)-2,5,8,11,14,23,26,29,32,35,38,41,44,47,50,53,56,59,62,69,72,75,78,85-tetracosaoxo-18,19,65,66,81,82-hexathia-3,6,9,12,15,22,25,28,31,34,37,40,43,46,49,52,55,58,61,70,73,76,79,84-tetracosazatricyclo[40.37.4.221,68]pentaoctacontan-24-yl]acetic acid
Canonical SMILES: C[C@H]1C(=O)N[C@H](C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)NCC(=O)N1)CCCCN)CCCCN)N)C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N3)CO)[C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC2=O)CO)CCCNC(=N)N)CC(C)C)CCSC)CC4=CC=C(C=C4)O)CC(=O)O)C(=O)N)CCCCN)CO)CCCNC(=N)N)CCCCN
InChI: InChI=1S/C102H172N36O32S7/c1-50(2)34-63-91(161)127-62(26-33-171-5)90(160)129-64(35-53-22-24-54(143)25-23-53)92(162)130-65(36-78(148)149)93(163)135-72-48-175-173-45-69(80(108)150)133-86(156)58(18-8-12-29-105)121-76(146)39-117-85(155)66(41-139)131-88(158)61(21-15-32-114-102(111)112)126-96(166)70-46-176-177-47-71(97(167)132-68(43-141)95(165)125-60(87(157)128-63)20-14-31-113-101(109)110)134-89(159)59(19-9-13-30-106)123-81(151)51(3)119-74(144)37-115-83(153)56(16-6-10-27-103)120-75(145)38-116-84(154)57(17-7-11-28-104)124-82(152)55(107)44-172-174-49-73(137-98(72)168)99(169)138-79(52(4)142)100(170)118-40-77(147)122-67(42-140)94(164)136-70/h22-25,50-52,55-73,79,139-143H,6-21,26-49,103-107H2,1-5H3,(H2,108,150)(H,115,153)(H,116,154)(H,117,155)(H,118,170)(H,119,144)(H,120,145)(H,121,146)(H,122,147)(H,123,151)(H,124,152)(H,125,165)(H,126,166)(H,127,161)(H,128,157)(H,129,160)(H,130,162)(H,131,158)(H,132,167)(H,133,156)(H,134,159)(H,135,163)(H,136,164)(H,137,168)(H,138,169)(H,148,149)(H4,109,110,113)(H4,111,112,114)/t51-,52+,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,79-/m0/s1
InChIKey: BPKIMPVREBSLAJ-QTBYCLKRSA-N

Cross-matching ID

PubChem CID: 16135415
ChEBI ID: CHEMBL4594214
CAS Number: 107452-89-1
UNII: 7I64C51O16
DrugBank ID: DB06283
TTD ID: D01NLB
INTEDE ID: DR1728

Drug-Molecule Activity Atlas (DMA)^NEW

Click to Jump to the Detailed DMA Information of This Drug

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Voltage-gated calcium channel alpha Cav2.2 (CACNA1B)	TT4FDG6	CAC1B_HUMAN	Blocker	[5]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[6]

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Pain

ICD Disease Classification

MG30-MG3Z

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Voltage-gated calcium channel alpha Cav2.2 (CACNA1B)	DTT	CACNA1B	9.07E-01	7.11E-03	0.06
Cytochrome P450 3A4 (CYP3A4)	DME	CYP3A4	8.31E-01	-4.19E-02	-2.14E-01

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Ziconotide and Esketamine.	Depression [6A70-6A7Z]	[7]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Ziconotide and Lasmiditan.	Migraine [8A80]	[8]

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2536).
2	Ziconotide FDA Label
3	FDA Approved Drug Products: Prialt (ziconotide) solution
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Emerging treatments for traumatic brain injury. Expert Opin Emerg Drugs. 2009 Mar;14(1):67-84.
6	Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
7	Cerner Multum, Inc. "Australian Product Information.".
8	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.