WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 318578
CAS#: 62666-20-0
Description: Progabide is an analog and prodrug of gamma-aminobutyric acid. It is commonly used in the treatment of epilepsy. Progabide has been investigated for many diseases besides epilepsy, including Parkinson's disease, schizophrenia, clinical depression and anxiety disorder with varying success.
MedKoo Cat#: 318578
Name: Progabide
CAS#: 62666-20-0
Chemical Formula: C17H16ClFN2O2
Exact Mass: 334.0884
Molecular Weight: 334.77
Elemental Analysis: C, 60.99; H, 4.82; Cl, 10.59; F, 5.68; N, 8.37; O, 9.56
Synonym: Progabide; Halogabide; Gabrene; Gabren; Progabida; Progabidum; progabide; SL 76002; DB00837; LS-45438;
IUPAC/Chemical Name: 4-[[(E)-(4-chlorophenyl)-(3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene)methyl]amino]butanamide
InChi Key: DWEQWXSKOHHBNT-VKAVYKQESA-N
InChi Code: InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14-
SMILES Code: C1=CC(=CC=C1C(=C2C=C(C=CC2=O)F)NCCCC(=O)N)Cl
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
| Biological target: | Progabide has agonistic activity for both the GABAA and GABAB receptors. |
| In vitro activity: | Progabide and other antiepileptic drugs were examined for their effects on corticosterone-induced gene transcription chloramphenicol acetyltransferase activity in mouse fibroblast cells. Progabide, alongside felbamate and loreclezole, inhibited glucocorticoid receptor-mediated transcription, potentially impacting antiepileptic drug efficacy and immune system function. Reference: Pharmacol Rep. 2007 Sep-Oct;59(5):531-7. https://pubmed.ncbi.nlm.nih.gov/18048953/ |
| In vivo activity: | This study investigated the effects of progabide on motor seizures induced by pentylenetetrazol in rats. The response to progabide varied with age: in adult rats, there was a tendency to suppress generalized tonic-clonic seizures, while in rat pups aged 7 to 18 days, progabide specifically suppressed the tonic phase of seizures. At 25 days of age, the only effect observed was an increase in the latency of major seizures at the highest progabide dose. Reference: Physiol Res. 1997;46(1):47-52. https://pubmed.ncbi.nlm.nih.gov/9728521/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 250.0 | 746.78 |
The following data is based on the product molecular weight 334.77 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. Basta-Kaim A, Budziszewska B, Leśkiewicz M, Regulska M, Otczyk M, Kubera M, Jagła G, Nowak W, Luszczki JJ, Czuczwar SJ, Lasoń W. Effects of some new antiepileptic drugs and progabide on glucocorticoid receptor-mediated gene transcription in LMCAT cells. Pharmacol Rep. 2007 Sep-Oct;59(5):531-7. PMID: 18048953. 2. Kroetz DL, Loiseau P, Guyot M, Levy RH. In vivo and in vitro correlation of microsomal epoxide hydrolase inhibition by progabide. Clin Pharmacol Ther. 1993 Nov;54(5):485-97. doi: 10.1038/clpt.1993.180. PMID: 8222491. 3. Stanková L, Kozuchová A, Mares P. Anticonvulsant effect of progabide in rats during ontogenesis. Physiol Res. 1997;46(1):47-52. PMID: 9728521. 4. Kaneda H, Shirakawa O, Dale J, Goodman L, Bachus SE, Tamminga CA. Co-administration of progabide inhibits haloperidol-induced oral dyskinesias in rats. Eur J Pharmacol. 1992 Feb 25;212(1):43-9. doi: 10.1016/0014-2999(92)90070-k. PMID: 1555638. |
| In vitro protocol: | 1. Basta-Kaim A, Budziszewska B, Leśkiewicz M, Regulska M, Otczyk M, Kubera M, Jagła G, Nowak W, Luszczki JJ, Czuczwar SJ, Lasoń W. Effects of some new antiepileptic drugs and progabide on glucocorticoid receptor-mediated gene transcription in LMCAT cells. Pharmacol Rep. 2007 Sep-Oct;59(5):531-7. PMID: 18048953. 2. Kroetz DL, Loiseau P, Guyot M, Levy RH. In vivo and in vitro correlation of microsomal epoxide hydrolase inhibition by progabide. Clin Pharmacol Ther. 1993 Nov;54(5):485-97. doi: 10.1038/clpt.1993.180. PMID: 8222491. |
| In vivo protocol: | 1. Stanková L, Kozuchová A, Mares P. Anticonvulsant effect of progabide in rats during ontogenesis. Physiol Res. 1997;46(1):47-52. PMID: 9728521. 2. Kaneda H, Shirakawa O, Dale J, Goodman L, Bachus SE, Tamminga CA. Co-administration of progabide inhibits haloperidol-induced oral dyskinesias in rats. Eur J Pharmacol. 1992 Feb 25;212(1):43-9. doi: 10.1016/0014-2999(92)90070-k. PMID: 1555638. |
1: Basta-Kaim A, Budziszewska B, Leśkiewicz M, Kubera M, Jagła G, Nowak W,
Czuczwar SJ, Lasoń W. Effects of new antiepileptic drugs and progabide on the
mitogen-induced proliferative activity of mouse splenocytes. Pharmacol Rep. 2008
Nov-Dec;60(6):925-32. PubMed PMID: 19211985.
2: Decourt JP, Mura P, Papet Y, Piriou A, Reiss D. Simultaneous determination of
progabide and its acid metabolite by reversed-phase high-performance liquid
chromatography. J Chromatogr. 1990 Apr 27;527(1):214-9. PubMed PMID: 2365784.
3: Mecarelli O, de Feo MR, Rina MF, Ricci GF. Effects of progabide on
bicuculline-induced epileptic seizures in developing rats. Clin Neuropharmacol.
1988 Oct;11(5):443-53. PubMed PMID: 3219676.
4: Farraj NF, Davis SS, Parr GD, Stevens HN. The stability and solubility of
progabide and its related metabolic derivatives. Pharm Res. 1988 Apr;5(4):226-31.
PubMed PMID: 3247302.
5: Stefan H, Plouin P, Fichsel H, Jalin C, Burr W. Progabide for previously
untreated absence epilepsy. Epilepsy Res. 1988 Mar-Apr;2(2):132-6. PubMed PMID:
3143558.
6: Brundage RC, Cloyd JC, Leppik IE, Graves NM, Welty TE. Effect of progabide on
serum phenytoin and carbamazepine concentrations. Clin Neuropharmacol. 1987
Dec;10(6):545-54. PubMed PMID: 3427561.
7: Cudennec A, Duverger D, Lloyd KG, MacKenzie ET, McCulloch J, Motohashi N,
Nishikawa T, Scatton B. Effects of the GABA receptor agonist, progabide, upon
local cerebral glucose utilization. Brain Res. 1987 Oct 13;423(1-2):162-72.
PubMed PMID: 2823984.
8: Koller WC, Rubino F, Gupta S. Pharmacologic probe with progabide of GABA
mechanisms in essential tremor. Arch Neurol. 1987 Sep;44(9):905-6. PubMed PMID:
3619708.
9: Luquin MR, Obeso JA, Scatton B, Lheroux A, Martinez Lage JM. Progabide in
Parkinson's disease. Ann Neurol. 1987 Aug;22(2):284-5. PubMed PMID: 3662460.
10: Ziegler M, Fournier V, Bathien N, Morselli PL, Rondot P. Therapeutic response
to progabide in neuroleptic- and L-dopa-induced dyskinesias. Clin Neuropharmacol.
1987 Jun;10(3):238-46. PubMed PMID: 2900682.
11: Hamberger C, Barre J, Brandebourger M, Urien S, Taiclet A, Thenot JP,
Tillement JP. Progabide and SL 75102 binding to plasma proteins and red blood
cells in humans. Int J Clin Pharmacol Ther Toxicol. 1987 Apr;25(4):178-84. PubMed
PMID: 3583466.
12: Bianchetti G, Padovani P, Thénot JP, Thiercelin JF, Morselli PL.
Pharmacokinetic interactions of progabide with other antiepileptic drugs.
Epilepsia. 1987 Jan-Feb;28(1):68-73. PubMed PMID: 3098557.
13: Mithani S, Atmadja S, Baimbridge KG, Fibiger HC. Neuroleptic-induced oral
dyskinesias: effects of progabide and lack of correlation with regional changes
in glutamic acid decarboxylase and choline acetyltransferase activities.
Psychopharmacology (Berl). 1987;93(1):94-100. PubMed PMID: 2888156.
14: Crawford P, Chadwick D. A comparative study of progabide, valproate, and
placebo as add-on therapy in patients with refractory epilepsy. J Neurol
Neurosurg Psychiatry. 1986 Nov;49(11):1251-7. PubMed PMID: 3098923; PubMed
Central PMCID: PMC1029073.
15: Ascalone V, Dal Bo' L. Chromatographic selectivity and maintenance of column
efficiency during the high-performance liquid chromatographic analysis of
progabide and its acid metabolite. J Chromatogr. 1986 Oct 31;382:412-4. PubMed
PMID: 3782413.
16: Schmidt D, Utech K. Progabide for refractory partial epilepsy: a controlled
add-on trial. Neurology. 1986 Feb;36(2):217-21. PubMed PMID: 3511402.
17: Mondrup K, Dupont E, Braendgaard H. Progabide in the treatment of
hyperkinetic extrapyramidal movement disorders. Acta Neurol Scand. 1985
Sep;72(3):341-3. PubMed PMID: 3864333.
18: Zivkovic B, Oblin A, Bartholini G. Progabide reverses the nigral substance P
reduction induced by chronic impairment of dopaminergic transmission. Eur J
Pharmacol. 1985 Jun 7;112(2):253-5. PubMed PMID: 2411575.
19: Di Scala G, Martin-Iverson MT, Phillips AG, Fibiger HC. The effects of
progabide (SL 76002) on locomotor activity and conditioned place preference
induced by d-amphetamine. Eur J Pharmacol. 1985 Jan 2;107(2):271-4. PubMed PMID:
2984007.
20: Martínez-Lage JM, Bossi L, Morales G, Martínez Vila E, Orofiamma B, Viteri C.
Progabide treatment in severe epilepsy: a double-blind cross-over trial versus
placebo. Epilepsia. 1984 Oct;25(5):586-93. PubMed PMID: 6383790.
