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Thiocolchicoside

Systematic (IUPAC) name
N-[(7S)-3-(beta-D-glucopyranosyloxy)-1,2-dimethoxy-10-(methylsulfanyl)-9-oxo-5,6,7,9-tetrahydrobenzo[a]heptalen-7-yl]acetamide
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	℞ Prescription only
Routes	Oral, Topical, IM
Pharmacokinetic data
Bioavailability	25%^[1]
Half-life	5-6 hours^[1]^[2]
Identifiers
CAS number	602-41-5
ATC code	M03BX05
PubChem	CID 72067
UNII	T1X8S697GT^Y
KEGG	D07276^Y
Chemical data
Formula	C₂₇H₃₃N O₁₀S
Mol. mass	563.618 g/mol
SMILES O=C(N[C@@H]4C1=C\C(=O)C(/SC)=C\C=C1c3c(cc(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO)c(OC)c3OC)CC4)C
InChI InChI=1S/C27H33NO10S/c1-12(30)28-16-7-5-13-9-18(37-27-24(34)23(33)22(32)19(11-29)38-27)25(35-2)26(36-3)21(13)14-6-8-20(39-4)17(31)10-15(14)16/h6,8-10,16,19,22-24,27,29,32-34H,5,7,11H2,1-4H3,(H,28,30)/t16?,19-,22-,23+,24-,27-/m1/s1 Key:LEQAKWQJCITZNK-MSQQGMGVSA-N
Y (what is this?) (verify)

Thiocolchicoside (Muscoril, Myoril, Neoflax) is a muscle relaxant with anti-inflammatory and analgesic effects.^[3]^[4]^[5]^[6] It acts as a competitive GABA_A receptor antagonist and also glycine receptor antagonist with similar potency and nicotinic acetylcholine receptors to a much lesser extent.^[7]^[8] It has powerful convulsant activity and should not be used in seizure-prone individuals.^[9]^[10]^[11]

Side effects [edit]

Side effect of skeletal muscle relaxants may include: sedation, drowsiness, blurred or double vision, constipation or diarrhea, dizziness and drowsiness, nervousness and confusion, dry mouth, dyspepsia (chronic or recurrent pain in the upper abdomen, upper abdominal fullness, and feeling full earlier than expected when eating), fatigue, headache, heartburn, hiccups and nausea, insomnia, stomach cramps, trembling, vomiting, and weakness; and possible dependence following long-term use.

References [edit]

^ ^a ^b Perucca E, Poitou P, Pifferi G (1995). "Comparative pharmacokinetics and bioavailability of two oral formulations of thiocolchicoside, a GABA-mimetic muscle relaxant drug, in normal volunteers". European Journal of Drug Metabolism and Pharmacokinetics 20 (4): 301–5. PMID 8983937.
^ Sandouk P, Bouvier d'Yvoire M, Chretien P, Tillement JP, Scherrmann JM (January 1994). "Single-dose bioavailability of oral and intramuscular thiocolchicoside in healthy volunteers". Biopharmaceutics & Drug Disposition 15 (1): 87–92. PMID 8161719.
^ Tüzün F, Unalan H, Oner N, et al. (September 2003). "Multicenter, randomized, double-blinded, placebo-controlled trial of thiocolchicoside in acute low back pain". Joint, Bone, Spine : Revue Du Rhumatisme 70 (5): 356–61. doi:10.1016/S1297-319X(03)00075-7. PMID 14563464.
^ Ketenci A, Basat H, Esmaeilzadeh S (July 2009). "The efficacy of topical thiocolchicoside (Muscoril) in the treatment of acute cervical myofascial pain syndrome: a single-blind, randomized, prospective, phase IV clinical study". Journal of the Turkish Society of Algology 21 (3): 95–103. PMID 19780000.
^ Soonawalla DF, Joshi N (May 2008). "Efficacy of thiocolchicoside in Indian patients suffering from low back pain associated with muscle spasm". Journal of the Indian Medical Association 106 (5): 331–5. PMID 18839644.
^ Ketenci A, Ozcan E, Karamursel S (July 2005). "Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain". International Journal of Clinical Practice 59 (7): 764–70. doi:10.1111/j.1742-1241.2004.00454.x. PMID 15963201.
^ Carta M, Murru L, Botta P, et al. (September 2006). "The muscle relaxant thiocolchicoside is an antagonist of GABAA receptor function in the central nervous system". Neuropharmacology 51 (4): 805–15. doi:10.1016/j.neuropharm.2006.05.023. PMID 16806306.
^ Mascia MP, Bachis E, Obili N, et al. (March 2007). "Thiocolchicoside inhibits the activity of various subtypes of recombinant GABA(A) receptors expressed in Xenopus laevis oocytes". European Journal of Pharmacology 558 (1-3): 37–42. doi:10.1016/j.ejphar.2006.11.076. PMID 17234181.
^ De Riu PL, Rosati G, Sotgiu S, Sechi G (August 2001). "Epileptic seizures after treatment with thiocolchicoside". Epilepsia 42 (8): 1084–6. doi:10.1046/j.1528-1157.2001.0420081084.x. PMID 11554898.
^ Giavina-Bianchi P, Giavina-Bianchi M, Tanno LK, Ensina LF, Motta AA, Kalil J (June 2009). "Epileptic seizure after treatment with thiocolchicoside". Therapeutics and Clinical Risk Management 5 (3): 635–7. PMC 2731019. PMID 19707540.
^ Sechi G, De Riu P, Mameli O, Deiana GA, Cocco GA, Rosati G (October 2003). "Focal and secondarily generalised convulsive status epilepticus induced by thiocolchicoside in the rat". Seizure : the Journal of the British Epilepsy Association 12 (7): 508–15. PMID 12967581.

Skeletal muscle relaxants (M03)

Peripherally acting
(primarily antinicotinic,
NMJ block)

Non-depolarizing

Curare alkaloids	Alcuronium Dimethyltubocurarine Tubocurarine

4° ammonium agents	ultra-short duration: Gantacurium short duration: Mivacurium Chandonium intermediate duration: Atracurium Cisatracurium Fazadinium Rocuronium Vecuronium long duration: Doxacurium Dimethyltubocurarine Pancuronium Pipecuronium Laudexium Gallamine unsorted: Hexafluronium (Hexafluorenium)

Depolarizing

Choline derivatives: Suxamethonium (Succinylcholine)

Polyalkylene derivatives: Hexamethonium

ACh release inhibitors

Botulinum toxin

Centrally acting

Carbamic acid esters	Carisoprodol Cyclarbamate Difebarbamate Febarbamate Meprobamate Methocarbamol Phenprobamate Styramate Tybamate

Benzodiazepines	Bentazepam Diazepam Clonazepam Flunitrazepam Lorazepam Nitrazepam Tetrazepam

Nonbenzodiazepines	Eszopiclone

Thienodiazepines	Etizolam

Quinazolines	Methaqualone

Anticholinergics (Antimuscarinics)	Cyclobenzaprine Orphenadrine

Other	Baclofen Chlormezanone Chlorphenesin Chlorzoxazone Donepezil Eperisone Fenyramidol Flopropione GHB Mephenesin Mephenoxalone Metaxalone Phenibut Pridinol Promoxolane Quinine Thiocolchicoside Tizanidine Tolperisone Trazodone

Directly acting

Dantrolene

M: MUS, DF+DRCT

anat (h/n, u, t/d, a/p, l)/phys/devp/hist

noco (m, s, c)/cong (d)/tumr, sysi/epon, injr

proc, drug (M1A/3)

Analgesics (N02A, N02B)

Opioids
See also: Opioids template

Opium & alkaloids thereof	Codeine^# Morphine^# Opium Laudanum Paregoric

Semi-synthetic opium derivatives	Acetyldihydrocodeine Benzylmorphine Buprenorphine Desomorphine Diacetylmorphine Dihydrocodeine Dihydromorphine Ethylmorphine Hydrocodone Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone Oxymorphone

Synthetic opioids	Alphaprodine Anileridine Butorphanol Dextromoramide Dextropropoxyphene Dezocine Fentanyl Ketobemidone Levorphanol Methadone Meptazinol Nalbuphine Pentazocine Propoxyphene Propiram Pethidine Phenazocine Piminodine Piritramide Tapentadol Tilidine Tramadol

Pyrazolones

Cannabinoids

Anilides

Non-steroidal
anti-inflammatories
See also: NSAIDs template

Propionic acid class	Fenoprofen Flurbiprofen Ibuprofen^# Ketoprofen Naproxen Oxaprozin

Oxicam class	Meloxicam Piroxicam

Acetic acid class	Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin

COX-2 inhibitors	Celecoxib Rofecoxib Valdecoxib Parecoxib Lumiracoxib

Anthranilic acid (fenamate) class	Meclofenamate Mefenamic acid

Salicylates	Aspirin (Acetylsalicylic acid)^# (+paracetamol/caffeine) Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Trisalate Wintergreen (Methyl salicylate)

Atypical, adjuvant and potentiators,
metabolic agents and miscellaneous

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: CNS

anat (n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco (m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug (N1A/2AB/C/3/4/7A/B/C/D)

Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)

Pyrazolidines

Salicylates

Acetic acid derivatives
and related substances

Oxicams

Propionic acid derivatives
(profens)

Alminoprofen
Benoxaprofen
Carprofen^‡
Dexibuprofen
Dexketoprofen
Fenbufen
Fenoprofen
Flunoxaprofen
Flurbiprofen
Ibuprofen
Ibuproxam
Indoprofen^†
Ketoprofen
Loxoprofen
Miroprofen
Naproxen
Oxaprozin
Pirprofen
Suprofen
Tarenflurbil
Tepoxalin^‡
Tiaprofenic acid
Vedaprofen^‡
COX-inhibiting nitric oxide donator: Naproxcinod

N-Arylanthranilic acids
(fenamates)

Coxibs

Other

Items listed in bold indicate initially developed compounds of specific groups. ^†Withdrawn drugs. ^‡Veterinary use medications.

M: MUS, DF+DRCT

anat (h/n, u, t/d, a/p, l)/phys/devp/hist

noco (m, s, c)/cong (d)/tumr, sysi/epon, injr

proc, drug (M1A/3)

GABAergics

Receptor
ligands

GABA_A	Agonists: Main site: Bamaluzole Gaboxadol Ibotenic acid Isoguvacine Isonipecotic acid Muscimol (Amanita Muscaria) Progabide SL 75102 Thiomuscimol Tolgabide; Positive allosteric modulators: Alcohols (2M2B, Ethanol, Ethchlorvynol, Methylpentynol Barbiturates Benzodiazepines Carbamates Chlormezanone Clomethiazole Etomidate Kavalactones (Kava) Loreclezole Metomidate Neuroactive steroids Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) Phenols Piperidinediones Propanidid Pyrazolopyridines Quinazolinones ROD-188 Skullcap Stiripentol Valerenic acid (Valerian) Note: See the GABA_A receptor PAMs navbox for a full list of GABA_A positive allosteric modulators. Antagonists: Main site: Bicuculline Gabazine Pitrazepin Quisqualamine; Negative allosteric modulators: 17-Phenylandrostenol (17-PA) α5IA Bilobalide Cicutoxin Cyclothiazide DMCM Flumazenil Flurothyl Furosemide Iomazenil (¹²³I) L-655,708 Oenanthotoxin Penicillin Pentylenetetrazol Picrotoxin PWZ-029 Radequinil Ro15-4513 Sarmazenil Suritozole Terbequinil Thujone Thiocolchicoside ZK-93426

GABA_B	Agonists: Main site: 1,4-Butanediol Baclofen GBL GHB GHV GVL Lesogaberan Phenibut Progabide SKF-97,541 Tolgabide; Positive allosteric modulators: BHF-177 BHFF BSPP CGP-7930 GS-39783 Antagonists: Main site: CGP-35348 Phaclofen Saclofen SCH-50911

GABA_C	Agonists: Main site: CACA CAMP GABOB N⁴-Chloroacetylcytosine arabinoside Progabide Tolgabide Antagonists: Main site: Bilobalide TPMPA

Reuptake
inhibitors

Plasmalemmal

GAT inhibitors	CI-966 Deramciclane EF-1502 Gabaculine Guvacine Nipecotic acid NNC 05-2090 SKF-89976A SNAP-5114 Tiagabine

Enzyme
inhibitors

Anabolism

GAD inhibitors	Allylglycine

Catabolism

GABA-T inhibitors	3-Hydrazinopropionic acid Aminooxyacetic acid Gabaculine Isoniazid Phenelzine Phenylethylidenehydrazine Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (Divalproex sodium) Valproic acid Valpromide Vigabatrin

Others

Precursors	Glutamate Glutamine

Cofactors	Vitamin B₆ (pyridoxine pyridoxamine pyridoxal phosphate)

Others	Gabapentin Hopantenic acid Picamilon Pregabalin L-Theanine

Glycinergics

Receptor
ligands

Agonists	Alanine Cycloserine Dimethylglycine Glycine Hypotaurine Methylglycine (Sarcosine) Milacemide Quisqualamine Serine Taurine Trimethylglycine (Betaine)

Antagonists	Bicuculline Brucine Caffeine Picrotoxin Pitrazepin Strychnine Thiocolchicoside Tutin

Reuptake
inhibitors

Plasmalemmal

GlyT1 inhibitors	Ethanol

GlyT2 inhibitors	Ethanol

Vesicular

VIAAT Inhibitors

Enzyme
inhibitors

Anabolism/Catabolism

SHMT Inhibitors

GDC Inhibitors

DAAO Inhibitors

Others

Precursors	3-Phosphoglyceric acid Serine

Cofactors	Vitamin B6 (Pyridoxine pyridoxamine pyridoxal → pyridoxal phosphate)

Cholinergics

Receptor ligands

mAChR	Agonists: 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B AFDX-384 Alvameline AQRA-741 Arecoline Bethanechol Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Ethoxysebacylcholine LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberylcholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796 Antagonists: 3-Quinuclidinyl Benzilate 4-DAMP Aclidinium Bromide Anisodamine Anisodine Atropine Atropine Methonitrate Benactyzine Benzatropine/Benztropine Benzydamine BIBN 99 Biperiden Bornaprine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Dimethindene Dexetimide DIBD Dicyclomine/Dicycloverine Ditran EA-3167 EA-3443 EA-3580 EA-3834 Etanautine Etybenzatropine/Ethylbenztropine Flavoxate Himbacine HL-031,120 Ipratropium bromide J-104,129 Hyoscyamine Mamba Toxin 3 Mamba Toxin 7 Mazaticol Mebeverine Methoctramine Metixene N-Ethyl-3-Piperidyl Benzilate N-Methyl-3-Piperidyl Benzilate Orphenadrine Otenzepad Oxybutynin PBID PD-102,807 PD-0298029 Phenglutarimide Phenyltoloxamine Pirenzepine Piroheptine Procyclidine Profenamine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine/Hyoscine Solifenacin Telenzepine Tiotropium bromide Tolterodine Trihexyphenidyl Tripitamine Tropatepine Tropicamide WIN-2299 Xanomeline Zamifenacin; Others: 1st Generation Antihistamines (Brompheniramine chlorphenamine cyproheptadine dimenhydrinate diphenhydramine doxylamine mepyramine/pyrilamine phenindamine pheniramine tripelennamine triprolidine, etc) Tricyclic Antidepressants (Amitriptyline doxepin trimipramine, etc) Tetracyclic Antidepressants (Amoxapine maprotiline, etc) Typical Antipsychotics (Chlorpromazine thioridazine, etc) Atypical Antipsychotics (Clozapine olanzapine, etc.)

nAChR	Agonists: 5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatoxin-a AR-R17779 Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Lobeline MEM-63,908/RG-3487 Nicotine NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline RJR-2429 Sazetidine A Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberylcholine Suxamethonium/Succinylcholine TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Antagonists: 18-Methoxycoronaridine α-Bungarotoxin α-Conotoxin Alcuronium Amantadine Anatruxonium Atracurium Bupropion Chandonium Chlorisondamine Cisatracurium Coclaurine Coronaridine Dacuronium Decamethonium Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dimethyltubocurarine/Metocurine Dipyrandium Dizocilpine/MK-801 Doxacurium Duador Esketamine Fazadinium Gallamine Hexafluronium Hexamethonium/Benzohexonium Ibogaine Isoflurane Ketamine Kynurenic acid Laudexium/Laudolissin Levacetylmethadol Malouetine Mecamylamine Memantine Methadone (Levomethadone) Methorphan/Racemethorphan Methyllycaconitine Metocurine Mivacurium Morphanol/Racemorphan Neramexane Nitrous Oxide Pancuronium Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium Radafaxine Rapacuronium Rocuronium Surugatoxin Thiocolchicoside Toxiferine Trimethaphan Tropeinium Tubocurarine Vecuronium Xenon

Reuptake inhibitors

Plasmalemmal

CHT Inhibitors	Hemicholinium-3/Hemicholine Triethylcholine

Vesicular

VAChT Inhibitors	Vesamicol

Enzyme inhibitors

Anabolism

ChAT inhibitors	1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate

Catabolism

AChE inhibitors	Reversible: Carbamates: Aldicarb Bendiocarb Bufencarb Carbaryl Carbendazim Carbetamide Carbofuran Chlorbufam Chloropropham Ethienocarb Ethiofencarb Fenobucarb Fenoxycarb Formetanate Furadan Ladostigil Methiocarb Methomyl Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur; Stigmines: Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine Rivastigmine; Others: Acotiamide Ambenonium Donepezil Caffeine Edrophonium Galantamine Huperzine A Minaprine Tacrine Zanapezil Irreversible: Organophosphates: Acephate Azinphos-methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-Methyl Coumaphos Cyclosarin Demeton Demeton-S-Methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimethoate Dioxathion Disulfoton EA-3148 Echothiophate Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate GV Isofluorophate Isoxathion Malaoxon Malathion Methamidophos Methidathion Metrifonate Mevinphos Monocrotophos Naled Novichok agent Omethoate Oxydemeton-Methyl Paraoxon Parathion Parathion-Methyl Phorate Phosalone Phosmet Phoxim Pirimiphos-Methyl Sarin Soman Tabun Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Onchidal (Onchidella binneyi)

BChE inhibitors	Cymserine * Many of the acetylcholinesterase inhibitors listed above act as butyrylcholinesterase inhibitors.

Others

Precursors	Choline (Lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate/Centrophenoxine Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

Cofactors	Acetic acid Acetylcarnitine Acetyl-coA Vitamin B₅ (Pantethine Pantetheine Panthenol)

Others	Acetylcholine releasing agents: α-Latrotoxin β-Bungarotoxin; Acetylcholine release inhibitors: Botulinum toxin (Botox); Acetylcholinesterase reactivators: Asoxime Obidoxime Pralidoxime

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Thiocolchicoside

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