Bucolome

Bucolome
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	none
Identifiers
IUPAC name 5-butyl-1-cyclohexyl-1,3-diazinane-2,4,6-trione
Synonyms	Bucolome, Paramidine
CAS Number	841-73-6
PubChem (CID)	2461
ChemSpider	2367^Y
UNII	9T08RAL174^Y
ChEBI	CHEBI:31314^Y
ChEMBL	CHEMBL2106136
ECHA InfoCard	100.011.515
Chemical and physical data
Formula	C₁₄H₂₂N₂O₃
Molar mass	224.256 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCC1C(=O)NC(=O)N(C1=O)C2CCCCC2
InChI InChI=1S/C14H22N2O3/c1-2-3-9-11-12(17)15-14(19)16(13(11)18)10-7-5-4-6-8-10/h10-11H,2-9H2,1H3,(H,15,17,19)^Y Key:DVEQCIBLXRSYPH-UHFFFAOYSA-N^Y
(verify)

Bucolome (Paramidine) is a barbiturate derivative. Unlike most barbiturates it does not have any significant sedative or hypnotic effects, but instead acts as an analgesic and antiinflammatory. It also acts as a CYP2C9 inhibitor and reduces the metabolism of several commonly used drugs, which makes it useful for potentiating or extending the duration of action of those drugs, or reducing the production of unwanted metabolites.^[1]^[2]^[3]

References

↑ Takamura N, Maruyama T, Chosa E, Kawai K, Tsutsumi Y, Uryu Y, Yamasaki K, Deguchi T, Otagiri M. Bucolome, a potent binding inhibitor for furosemide, alters the pharmacokinetics and diuretic effect of furosemide: potential for use of bucolome to restore diuretic response in nephrotic syndrome. Drug Metabolism and Disposition. 2005 Apr;33(4):596-602. PMID 15640375
↑ Osawa M, Hada N, Matsumoto K, Hasegawa T, Kobayashi D, Morimoto Y, Yamaguchi M, Kanamoto I, Nakagawa T, Sugibayashi K. Usefulness of coadministration of bucolome in warfarin therapy: pharmacokinetic and pharmacodynamic analysis using outpatient prescriptions. International Journal of Pharmaceutics. 2005 Apr 11;293(1-2):43-9. PMID 15778043
↑ Kobayashi M, Takagi M, Fukumoto K, Kato R, Tanaka K, Ueno K. The effect of bucolome, a CYP2C9 inhibitor, on the pharmacokinetics of losartan. Drug Metabolism and Pharmacokinetics. 2008;23(2):115-9. PMID 18445991

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine^# (+paracetamol, +aspirin) Morphine^# (+naltrexone) Opium Laudanum Paregoric

Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Thebacon

Synthetic	Alphaprodine Anileridine Butorphanol Dextromoramide Dextropropoxyphene Dezocine Fentanyl (+fluanisone) Ketobemidone Levorphanol Meptazinol Methadone Nalbuphine Pentazocine Pethidine Phenadoxone Phenazocine Piminodine Piritramide Propiram Tapentadol Tilidine Tramadol

Paracetamol-type

Acetanilide^‡
Bucetin^‡
Butacetin^‡
Paracetamol (acetaminophen)^#
Parapropamol^‡
Phenacetin^‡
Propacetamol^‡

NSAIDs

Propionates	Fenoprofen Flurbiprofen Ibuprofen^# Ketoprofen Naproxen Oxaprozin

Oxicams	Meloxicam Piroxicam

Acetates	Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin

COX-2 inhibitors	Celecoxib Etoricoxib Lumiracoxib Parecoxib Rofecoxib ^‡ Valdecoxib ^‡

Fenamates	Meclofenamic acid Mefenamic acid

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

Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone

Others	Glafenine

Cannabinoids

Ion channel
modulators

Calcium blockers	Gabapentin Gabapentin enacarbil Pregabalin Ziconotide

Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g., cocaine, lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g., amitriptyline^#) Na_v1.7/1.8-selective: DSP-2230^§ Funapide^§ PF-05089771^§ Raxatrigine^§

Potassium openers	Flupirtine

Myorelaxants

Others

Camphor
Capsaicin
Clonidine
Ketamine
Menthol
Methoxyflurane
Nefopam
Proglumide
Tricyclic antidepressants (e.g., amitriptyline^#)

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

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

Pyrazolones / Pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡

Salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate

Acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bumadizone Bufexamac Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indomethacin Indomethacin farnesil Isoxepac Ketorolac Lonazolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†

Oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam

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)	Azapropazone Clonixin Etofenamate Flufenamic acid Flunixin Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid Flutiazin

Coxibs	Apricoxib Celecoxib Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†

Other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase/Orgotein Tenidap

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

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