Details of the Drug

General Information of Drug (ID: DM6T924)

Drug Name

Gabapentin

Synonyms

Aclonium; GBN; Gabapen; Gabapentina; Gabapentine; Gabapentinium; Gabapentino; Gabapentinum; Gabapetin; Neurontin; Serada; Vultin; Apotex brand of gabapentin; Aventis brand of gabapentin; Gabapentin GR; Gabapentin Hexal; Gabapentin Stada; Gabapentino [Spanish]; Hexal brand of gabapentin; Novopharm brand of gabapentin; Parke Davis brand of gabapentin; Pfizer brand of gabapentin; Pharmascience brand of gabapentin; Ratiopharm brand of gabapentin; Stadapharm brand of gabapentin; GOE 2450; Go 3450; Apo-Gabapentin; DDS-2003; DM-1796; DM-5689; G-154; Gabapentin (Neurontin); Gabapentin-ratiopharm; Gabapentine [INN-French]; Gabapentino [INN-Spanish]; Gabapentinum [INN-Latin]; Goe-3450; Neurontin (TN); Novo-Gabapentin; PMS-Gabapentin; Warner-Lambert brand of gabapentin; Gabapentin [USAN:INN:BAN]; [1-(AMINOMETHYL)CYCLOHEXYL]ACETIC ACID; Gabapentin (JAN/USAN/INN); 1-(Aminomethyl)-cyclohexaneacetic acid; 1-(Aminomethyl)cyclohexaneacetic acid; 2-[1-(aminomethyl)cyclohexyl]acetic acid

Indication

Disease Entry	ICD 11	Status	REF
Complex partial seizure	8A68.0	Approved	[1]
Postherpetic neuralgia	1E91.5	Approved	[2]
Solid tumour/cancer	2A00-2F9Z	Phase 3	[1]

Therapeutic Class

Analgesics

Affected Organisms

Humans and other mammals

ATC Code

N02BF01: Gabapentin

N02BF: Gabapentinoids

N02B: OTHER ANALGESICS AND ANTIPYRETICS

N02: ANALGESICS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

171.24

Logarithm of the Partition Coefficient (xlogp)

-1.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 370 to 650 mcg/L [3]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [4]
Bioavailability: The bioavailability of drug is 11% [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 1.7 mL/min/kg [5]
Elimination: Cimetidine, an inhibitor of renal tubular secretion, reduces clearance by approximately 12%, suggesting that some degree of tubular secretion is involved in the renal elimination of gabapentin [6]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 - 7 hours (in patients with normal renal function), and 52 hours (in patients with reduced renal function) [7]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 116.79423 micromolar/kg/day [8]
Unbound Fraction: The unbound fraction of drug in plasma is 0.97% [5]
Vd: The volume of distribution (Vd) of drug is 58 +/- 6 L [7]
Water Solubility: The ability of drug to dissolve in water is measured as 10 mg/mL [4]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Akathisia	Not Available	DRD1	OTLZPBT7	[9]
Diabetic complications renal	Not Available	GFPT1	OTQBDO45	[9]
Diabetic complications renal	Not Available	TGFB1	OTV5XHVH	[9]
Sleep disturbances (incl subtypes)	Not Available	HTR3A	OTAIV1AK	[9]
Sleep disturbances (incl subtypes)	Not Available	HTR2B	OTM1AD9J	[9]
Sleep disturbances (incl subtypes)	Not Available	ADRA1A	OTUIWCL5	[9]
Sleep disturbances (incl subtypes)	Not Available	HTR2A	OTWXJX0M	[9]


⏷ Show the Full List of 7 ADR Information of This Drug

Chemical Identifiers

Formula: C9H17NO2
IUPAC Name: 2-[1-(aminomethyl)cyclohexyl]acetic acid
Canonical SMILES: C1CCC(CC1)(CC(=O)O)CN
InChI: InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChIKey: UGJMXCAKCUNAIE-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 3446
ChEBI ID: CHEMBL940
CAS Number: 60142-96-3
UNII: 6CW7F3G59X
DrugBank ID: DB00996
TTD ID: D0J0ZS
VARIDT ID: DR00217
ACDINA ID: D00296

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Combinatorial Drugs (CBD)

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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
Gamma-aminobutyric acid B receptor (GABBR)	TTDCVZW	GABR1_HUMAN ; GABR2_HUMAN	Antagonist	[10]

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
L-type amino acid transporter 1 (SLC7A5)	DT48T0N	LAT1_HUMAN	Substrate	[11]
Organic cation/carnitine transporter 1 (SLC22A4)	DT2EG60	S22A4_HUMAN	Substrate	[12]
Organic cation transporter 2 (SLC22A2)	DT9IDPW	S22A2_HUMAN	Substrate	[13]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
5-hydroxytryptamine receptor 2A (HTR2A)	OTWXJX0M	5HT2A_HUMAN	Drug Response	[9]
5-hydroxytryptamine receptor 2B (HTR2B)	OTM1AD9J	5HT2B_HUMAN	Drug Response	[9]
5-hydroxytryptamine receptor 3A (HTR3A)	OTAIV1AK	5HT3A_HUMAN	Drug Response	[9]
Alpha-1A adrenergic receptor (ADRA1A)	OTUIWCL5	ADA1A_HUMAN	Drug Response	[9]
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Gene/Protein Processing	[14]
D(1A) dopamine receptor (DRD1)	OTLZPBT7	DRD1_HUMAN	Drug Response	[9]
Glutamine--fructose-6-phosphate aminotransferase 1 (GFPT1)	OTQBDO45	GFPT1_HUMAN	Drug Response	[9]
SH3 and multiple ankyrin repeat domains protein 2 (SHANK2)	OTSQTPFQ	SHAN2_HUMAN	Gene/Protein Processing	[15]
Sodium-dependent serotonin transporter (SLC6A4)	OT6FGDLW	SC6A4_HUMAN	Gene/Protein Processing	[15]
Transforming growth factor beta-1 proprotein (TGFB1)	OTV5XHVH	TGFB1_HUMAN	Drug Response	[9]

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 Gabapentin (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Dihydrocodeine	DMB0FWL	Major	Additive CNS depression effects by the combination of Gabapentin and Dihydrocodeine.	Chronic pain [MG30]	[16]
Sertraline	DM0FB1J	Moderate	Antagonize the effect of Gabapentin when combined with Sertraline.	Depression [6A70-6A7Z]	[17]
Vilazodone	DM4LECQ	Moderate	Antagonize the effect of Gabapentin when combined with Vilazodone.	Depression [6A70-6A7Z]	[17]
Vortioxetine	DM6F1PU	Moderate	Antagonize the effect of Gabapentin when combined with Vortioxetine.	Depression [6A70-6A7Z]	[17]
Milnacipran	DMBFE74	Moderate	Antagonize the effect of Gabapentin when combined with Milnacipran.	Depression [6A70-6A7Z]	[17]
Escitalopram	DMFK9HG	Moderate	Antagonize the effect of Gabapentin when combined with Escitalopram.	Depression [6A70-6A7Z]	[17]
Desvenlafaxine	DMHD4PE	Moderate	Antagonize the effect of Gabapentin when combined with Desvenlafaxine.	Depression [6A70-6A7Z]	[17]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Gabapentin and Esketamine.	Depression [6A70-6A7Z]	[18]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Gabapentin and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[19]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Gabapentin and Lasmiditan.	Migraine [8A80]	[20]
Flibanserin	DM70DTN	Moderate	Additive CNS depression effects by the combination of Gabapentin and Flibanserin.	Mood disorder [6A60-6E23]	[21]
Thalidomide	DM70BU5	Moderate	Additive CNS depression effects by the combination of Gabapentin and Thalidomide.	Multiple myeloma [2A83]	[22]
Levomethadyl Acetate	DM06HG5	Major	Additive CNS depression effects by the combination of Gabapentin and Levomethadyl Acetate.	Opioid use disorder [6C43]	[16]
Oxymorphone	DM65AGJ	Major	Additive CNS depression effects by the combination of Gabapentin and Oxymorphone.	Pain [MG30-MG3Z]	[23]
Dezocine	DMJDB0Y	Major	Additive CNS depression effects by the combination of Gabapentin and Dezocine.	Pain [MG30-MG3Z]	[23]


⏷ Show the Full List of 15 DDI Information of This Drug

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
Calcium carbonate	E00198	10112	Binding agent; Buffering agent; Diluent; Opacifying agent
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Hydrazine yellow	E00409	164825	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Aluminum trihydroxide	E00505	10176082	Alkalizing agent; Vaccine adjuvant
Ammonia	E00007	222	Alkalizing agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Brushite	E00392	104805	Diluent
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Calcium stearate	E00244	15324	lubricant
Calcium sulfate dihydrate	E00315	24928	Desiccant; Diluent
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
FD&C red no. 3	E00629	Not Available	Colorant
Ferric hydroxide oxide yellow	E00539	23320441	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Gelatin	E00630	Not Available	Other agent
Glyceryl behenate	E00481	5362585	Binding agent; Coating agent; Flavoring agent; Modified-release agent; Viscosity-controlling agent; lubricant
Glyceryl dibehenate	E00537	22477175	Binding agent; Coating agent; Flavoring agent; Modified-release agent; Viscosity-controlling agent; lubricant
Hypromellose	E00634	Not Available	Coating agent
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Poloxamer 407	E00646	Not Available	Emulsifying agent; Solubilizing agent; Surfactant
Polyethylene glycol 3350	E00652	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; 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
Potassium hydroxide	E00233	14797	Alkalizing agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Propylene glycol distearate	E00395	110800	Emollient; Opacifying agent; Surfactant
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium hydroxide	E00234	14798	Alkalizing agent
Soybean lecithin	E00637	Not Available	Other agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent


⏷ Show the Full List of 45 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Gabapentin 400 mg capsule	400 mg	Oral Capsule	Oral
Gabapentin 300 mg capsule	300 mg	Oral Capsule	Oral
Gabapentin 100 mg capsule	100 mg	Oral Capsule	Oral
Gabapentin 300 mg tablet	300 mg	Extended Release Oral Tablet	Oral
Gabapentin 600 mg tablet	600 mg	24 HR Extended Release Tablet	Oral
Gabapentin Enacarbil 300mg extended release tablet	300mg	Extended Release Tablet	Oral
Gabapentin Enacarbil 600mg extended release tablet	600mg	Extended Release Tablet	Oral
Gabapentin 600 mg tablet	600 mg	Oral Tablet	Oral
Gabapentin 800 mg tablet	800 mg	Oral Tablet	Oral
Gabapentin 100 mg tablet	100 mg	Oral Tablet	Oral
Gabapentin 300 mg tablet	300 mg	Oral Tablet	Oral
Gabapentin 400 mg tablet	400 mg	Oral Tablet	Oral

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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: 5483).
2	Gabapentin FDA Label
3	FDA Approved Drug Products: CAMPRAL (acamprosate calcium) delayed-release tablets
4	BDDCS applied to over 900 drugs
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Bockbrader HN, Wesche D, Miller R, Chapel S, Janiczek N, Burger P: A comparison of the pharmacokinetics and pharmacodynamics of pregabalin and gabapentin. Clin Pharmacokinet. 2010 Oct;49(10):661-9. doi: 10.2165/11536200-000000000-00000.
7	FDA Approved Drug Products: Neurontin (gabapentin) for oral use
8	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
9	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
10	Gabapentin increases a tonic inhibitory conductance in hippocampal pyramidal neurons. Anesthesiology. 2006 Aug;105(2):325-33.
11	Transport of gabapentin by LAT1 (SLC7A5). Biochem Pharmacol. 2013 Jun 1;85(11):1672-83.
12	Effects of genetic variation in the novel organic cation transporter, OCTN1, on the renal clearance of gabapentin. Clin Pharmacol Ther. 2008 Mar;83(3):416-21.
13	Clinical pharmacokinetic drug interaction studies of gabapentin enacarbil, a novel transported prodrug of gabapentin, with naproxen and cimetidine. Br J Clin Pharmacol. 2010 May;69(5):498-507.
14	Functional evaluation of polymorphisms in the human ABCB1 gene and the impact on clinical responses of antiepileptic drugs. Pharmacogenet Genomics. 2008 May;18(5):390-402. doi: 10.1097/FPC.0b013e3282f85e36.
15	Establishment of a 13 genes-based molecular prediction score model to discriminate the neurotoxic potential of food relevant-chemicals. Toxicol Lett. 2022 Feb 1;355:1-18. doi: 10.1016/j.toxlet.2021.10.013. Epub 2021 Nov 5.
16	Eipe N, Penning J "Postoperative respiratory depression associated with pregabalin: a case series and a preoperative decision algorithm." Pain Res Manag 16 (2011): 353-6. [PMID: 22059207]
17	Belcastro V, Costa C, Striano P "Levetiracetam-associated hyponatremia." Seizure 17 (2008): 389-90. [PMID: 18584781]
18	Cerner Multum, Inc. "Australian Product Information.".
19	Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
20	Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
21	Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
22	Product Information. Thalomid (thalidomide). Celgene Corporation, Warren, NJ.
23	Eckhardt K, Ammon S, Hofmann U, Riebe A, Gugeler N, Mikus G "Gabapentin enhances the analgesic effect of morphine in healthy volunteers." Anesth Analg 91 (2000): 185-91. [PMID: 10866910]