Ibrolipim: Difference between revisions

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	{{~~chembox~~		{{Chembox
			\| Verifiedfields = changed
			\| verifiedrevid = 461775154
		⚫	\| ImageFile = Ibrolipim structure.svg
		⚫	\| ImageSize = 120
		⚫	\| PIN = Diethyl ({4-phenyl}methyl)phosphonate
		⚫	\| OtherNames =
		⚫	\|Section1={{Chembox Identifiers
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = 07H1561618		\| UNII = 07H1561618
		⚫	\| InChI = 1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
⚫	\| ImageFile = Ibrolipim structure.~~png~~
⚫	\| ImageSize = 120
⚫	\| ~~IUPACName~~ = ~~diethyl~~ {4-~~benzyl~~}phosphonate
⚫	\| OtherNames =
⚫	\| Section1 = {{Chembox Identifiers
⚫	\| InChI = 1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
	\| InChIKey1 = KPRTURMJVWXURQ-UHFFFAOYSA-N		\| InChIKey1 = KPRTURMJVWXURQ-UHFFFAOYSA-N
	\| InChI1 = 1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)		\| InChI1 = 1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo =
	\| ~~PubChem~~ = ~~131601~~		\| CASNo = 133208-93-2
	\| ~~ChemSpiderID~~ = ~~116297~~		\| PubChem = 131601
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
			\| ChemSpiderID = 116297
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D03747		\| KEGG = D03747
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = KPRTURMJVWXURQ-UHFFFAOYSA-N		\| StdInChIKey = KPRTURMJVWXURQ-UHFFFAOYSA-N
	\| SMILES = Brc2cc(C#N)c(NC(=O)c1ccc(cc1)CP(=O)(OCC)OCC)cc2		\| SMILES = Brc2cc(C#N)c(NC(=O)c1ccc(cc1)CP(=O)(OCC)OCC)cc2
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = ~~StdInChI=~~1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)		\| StdInChI = 1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
	\| Formula = C19H20BrN2O4P
			\| Formula = C<sub>19</sub>H<sub>20</sub>BrN<sub>2</sub>O<sub>4</sub>P
	\| MolarMass = 451.25
	\| ~~Appearance~~ =		\| MolarMass = 451.25
	\| ~~Density~~ =		\| Appearance =
	\| ~~MeltingPt~~ =		\| Density =
	\| ~~BoilingPt~~ =		\| MeltingPt =
	\| ~~Solubility~~ =		\| BoilingPt =
			\| Solubility =
	}}		}}
	\| Section3 = {{Chembox Hazards		\|Section3={{Chembox Hazards
	\| MainHazards =
	\| ~~FlashPt~~ =		\| MainHazards =
	\| ~~Autoignition~~ =		\| FlashPt =
			\| AutoignitionPt =
	}}		}}
	}}		}}

	'''Ibrolipim''' ('''NO-1886''') is a ] lowering drug from the ] family, which acts as a ] activator. The discovery of the ~~“statin”~~ mevalonic acid synthesis inhibitors focused new attention on control of blood lipid levels as a measure to stave off heart disease. A number of compounds have been found that treat elevated lipid levels by other diverse mechanisms. The phosphonic acid derivative ibrolipim is believed to lower those levels by accelerating fatty acid oxidation.<ref name="pmid12847564">{{cite journal \|~~author~~=Yin W, Tsutsumi K \|title=Lipoprotein lipase activator NO-1886 \|journal=Cardiovascular Drug Reviews \|volume=21 \|issue=2 \|pages=133–42 \|year=2003 \|pmid=12847564 \|doi= \|~~url~~=}}</ref>		'''Ibrolipim''' ('''NO-1886''') is a ] lowering drug from the ] family, which acts as a ] activator. The discovery of the "statin" mevalonic acid synthesis inhibitors focused new attention on control of blood lipid levels as a measure to stave off heart disease. A number of compounds have been found that treat elevated lipid levels by other diverse mechanisms. The phosphonic acid derivative ibrolipim is believed to lower those levels by accelerating fatty acid oxidation.<ref name="pmid12847564">{{cite journal \|vauthors=Yin W, Tsutsumi K \|title=Lipoprotein lipase activator NO-1886 \|journal=Cardiovascular Drug Reviews \|volume=21 \|issue=2 \|pages=133–42 \|year=2003 \|pmid=12847564 \|doi= 10.1111/j.1527-3466.2003.tb00111.x\|doi-access=free }}</ref>


	==References==		==References==
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Latest revision as of 18:46, 30 January 2023

Ibrolipim
Names

Preferred IUPAC name Diethyl ({4-phenyl}methyl)phosphonate
Identifiers
CAS Number	133208-93-2
3D model (JSmol)	Interactive image
ChemSpider	116297
ECHA InfoCard	100.162.319
KEGG	D03747
PubChem CID	131601
UNII	07H1561618
CompTox Dashboard (EPA)	DTXSID20157989
InChI InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)Key: KPRTURMJVWXURQ-UHFFFAOYSA-N InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23) InChI=1S/C19H20BrN2O4P/c1-3-25-27(24,26-4-2)13-14-5-7-15(8-6-14)19(23)22-18-10-9-17(20)11-16(18)12-21/h5-11H,3-4,13H2,1-2H3,(H,22,23)Key: KPRTURMJVWXURQ-UHFFFAOYSA-N
SMILES Brc2cc(C#N)c(NC(=O)c1ccc(cc1)CP(=O)(OCC)OCC)cc2
Properties
Chemical formula	C₁₉H₂₀BrN₂O₄P
Molar mass	451.25
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Ibrolipim (NO-1886) is a cholesterol lowering drug from the statin family, which acts as a lipoprotein lipase activator. The discovery of the "statin" mevalonic acid synthesis inhibitors focused new attention on control of blood lipid levels as a measure to stave off heart disease. A number of compounds have been found that treat elevated lipid levels by other diverse mechanisms. The phosphonic acid derivative ibrolipim is believed to lower those levels by accelerating fatty acid oxidation.

References

Yin W, Tsutsumi K (2003). "Lipoprotein lipase activator NO-1886". Cardiovascular Drug Reviews. 21 (2): 133–42. doi:10.1111/j.1527-3466.2003.tb00111.x. PMID 12847564.

v t e Major chemical drug groups – based upon the Anatomical Therapeutic Chemical Classification System
gastrointestinal tract / metabolism (A)	stomach acid Antacids H₂ antagonists Proton-pump inhibitors Antiemetics Laxatives Antidiarrhoeals / Antipropulsives Anti-obesity drugs Diabetes medication Vitamins Dietary minerals
blood and blood forming organs (B)	Antithrombotics Antiplatelets Anticoagulants Thrombolytics / fibrinolytics Antihemorrhagics Platelets Coagulants Antifibrinolytics
cardiovascular system (C)	cardiac therapy / antianginals Cardiac glycosides Antiarrhythmics Cardiac stimulants Antihypertensives Diuretics Vasodilators Beta blockers Calcium channel blockers renin–angiotensin system ACE inhibitors Angiotensin II receptor antagonists Renin inhibitors Antihyperlipidemics Statins Fibrates Bile acid sequestrants
skin (D)	Emollients Cicatrizants Antipruritics Antipsoriatics Medicated dressings
genitourinary system (G)	Hormonal contraception Fertility agents Selective estrogen receptor modulators Sex hormones
endocrine system (H)	Hypothalamic–pituitary hormones Corticosteroids Glucocorticoids Mineralocorticoids Sex hormones Thyroid hormones / Antithyroid agents
infections and infestations (J, P, QI)	Antimicrobials: Antibacterials (Antimycobacterials) Antifungals Antivirals Antiparasitics Antiprotozoals Anthelmintics Ectoparasiticides Intravenous immunoglobulin Vaccines
malignant disease (L01–L02)	Anticancer agents Antimetabolites Alkylating Spindle poisons Antineoplastic Topoisomerase inhibitors
immune disease (L03–L04)	Immunomodulators Immunostimulants Immunosuppressants
muscles, bones, and joints (M)	Anabolic steroids Anti-inflammatories Non-steroidal anti-inflammatory drugs Antirheumatics Corticosteroids Muscle relaxants Bisphosphonates
brain and nervous system (N)	Analgesics Anesthetics General Local Anorectics Anti-ADHD agents Antiaddictives Anticonvulsants Antidementia agents Antidepressants Antimigraine agents Antiparkinson agents Antipsychotics Anxiolytics Aphrodisiacs Depressants Entactogens Entheogens Euphoriants Hallucinogens Psychedelics Dissociatives Deliriants Hypnotics / Sedatives Mood stabilizers Motivation-enhancing drug Neuroprotectives Nootropics Neurotoxins Orexigenics Serenics Stimulants Wakefulness-promoting agents
respiratory system (R)	Decongestants Bronchodilators Cough medicines H₁ antagonists
sensory organs (S)	Ophthalmologicals Otologicals
other ATC (V)	Antidotes Contrast media Radiopharmaceuticals Dressings Senotherapeutics
Drugs Pharmacological classification systems ATC codes Medicine portal

Lipid-lowering agents (C10)

GI tract

Cholesterol absorption inhibitors, NPC1L1	Ezetimibe Hyzetimibe SCH-48461
Bile acid sequestrants/resins (LDL)	Colesevelam Colestilan Colestipol Colestyramine Colextran Soluble fiber such as psyllium and glucomannan

Liver

Statins (HMG-CoA reductase, LDL)	Atorvastatin Cerivastatin Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin
Niacin and derivatives (HDL and LDL)	Acipimox Aluminium nicotinate Niacin Niceritrol Nicofuranose Nicotinyl alcohol
MTTP inhibitors (VLDL)	Dirlotapide Lomitapide Mitratapide
ATP citrate lyase inhibitors (LDL)	Bempedoic acid
Thyromimetics (VLDL)	Dextrothyroxine Resmetirom

Blood vessels

PPAR agonists (LDL)

Fibrates	Aluminium clofibrate Bezafibrate Choline fenofibrate Ciprofibrate Clinofibrate Clofibrate Clofibride Etofibrate Fenofibrate Gemfibrozil Nafenopin Pemafibrate Ronifibrate Simfibrate
Others	GW501516

CETP inhibitors (HDL)

PCSK9 inhibitors (LDL)

ANGPTL3 inhibitors (LDL/HDL)

Evinacumab

Combinations

Other

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Categories: