Nitrosoprodenafil

Nitrosoprodenafil
Clinical data

Routes of administration	oral
ATC code	None
Identifiers
IUPAC name 2-[(5-[5-(3,5-Dimethylpiperazine-1-sulfonyl)-2-ethoxyphenyl]-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl)oxy]-N-methyl-N-nitroso-1,3-thiazol-5-amine
CAS Number	1266755-08-1
PubChem CID	71308247
ChemSpider	32701496
UNII	X8TO9P16G7
CompTox Dashboard (EPA)	DTXSID301029943
Chemical and physical data
Formula	C₂₈H₃₈N₈O₅S₂
Molar mass	630.78 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCc1c2c(c(nc(n2)c3cc(ccc3OCC)S(=O)(=O)N4C[C@H](N[C@H](C4)C)C)Oc5ncc(s5)N(C)N=O)n(n1)C
InChI InChI=1S/C27H35N9O5S2/c1-7-9-20-23-24(35(6)32-20)26(41-27-28-13-22(42-27)34(5)33-37)31-25(30-23)19-12-18(10-11-21(19)40-8-2)43(38,39)36-14-16(3)29-17(4)15-36/h10-13,16-17,29H,7-9,14-15H2,1-6H3/t16-,17+ Key:DTAKXJYYAUWRND-CALCHBBNSA-N

Nitrosoprodenafil is a synthetic designer drug found in "herbal" aphrodisiac products, which is a novel nitrosated analogue of sildenafil (Viagra). It has an innovative structure which acts as a prodrug, breaking down in the body to release both the PDE₅ inhibitor aildenafil as well as free nitric oxide, which have powerfully synergistic effects. This dual mechanism of action has never been exploited by conventional pharmaceutical companies because of the risks involved; usually combining PDE₅ inhibitors with nitric oxide releasers like amyl nitrite is contraindicated as it can cause a precipitous drop in blood pressure that can potentially result in death. Nitrosamines are also generally avoided in drug development as they can often be hepatotoxic and carcinogenic, so while the combined mechanisms of action are likely to be effective, this drug also has severe risks of toxicity.^[1]

Shortly after Venhuis et al. published the suggested structure for nitrosoprodenafil, it was contested by Demizu et al. who suggested the structure was an azathioprine/aildenafil hybrid.^[2] This newly suggested structure was dubbed 'mutaprodenafil' because of the structural similarity with the mutagenic immunosuppressive drug azathioprine.

The final confirmation of the azathioprine/aildenafil hybrid was provided by Sakamoto et al. who prepared crystals for X-ray analysis.^[3] Although Sakamoto et al. support the name 'mutaprodenafil', they prefer to use 'nitrosoprodenafil' instead.

References

^ Venhuis BJ, Zomer G, Hamzink M, Meiring HD, Aubin Y, de Kaste D (March 2011). "The identification of a nitrosated prodrug of the PDE-5 inhibitor aildenafil in a dietary supplement: a Viagra with a pop". Journal of Pharmaceutical and Biomedical Analysis. 54 (4): 735–41. doi:10.1016/j.jpba.2010.11.020. PMID 21145686.
^ Demizu Y, Wakana D, Kamakura H, Kurihara M, Okuda H, Goda Y (2011). "Identification of mutaprodenafil in a dietary supplement and its subsequent synthesis". Chemical & Pharmaceutical Bulletin. 59 (10): 1314–6. doi:10.1248/cpb.59.1314. PMID 21963647.
^ Sakamoto M, Moriyasu T, Minowa K, Kishimoto K, Kadoi H, Hamano T, Fukaya H (2012). "Structure elucidation of a novel analog of sildenafil detected as an adulterant in a dietary supplement using LC-UV and LC/MS". Journal of AOAC International. 95 (4): 1048–52. doi:10.5740/jaoacint.11-235. PMID 22970570.

v t e Sexual dysfunction pharmacotherapies
Dopamine agonists	Apomorphine Cabergoline Lisuride Pergolide Piribedil Pramipexole Quinagolide Ropinirole Rotigotine Terguride
Melanocortin agonists	Bremelanotide Melanotan II PL-6983
PDE5 inhibitors	Acetildenafil Aildenafil Avanafil Icariin Lodenafil Mirodenafil Nitrosoprodenafil Sildenafil Sulfoaildenafil Tadalafil Udenafil Vardenafil
Sex steroids	Androgens (e.g., testosterone, methyltestosterone, other anabolic steroids) Estrogens (e.g., estradiol, ethinylestradiol, conjugated equine estrogens (Premarin)) Progestogens (e.g., progesterone, progestins) Mixed (e.g., tibolone)
Others	Afrodor (acecarbromal, quebracho, vitamin E) Alkyl nitrites Alprostadil Amantadine Bupropion Buspirone Cyproheptadine Dapoxetine Flibanserin Mirtazapine Moxisylyte Oxytocin Papaverine Phentolamine Psychostimulants (e.g., amphetamines, cocaine, methylphenidate) Rauwolscine (Rauvolfia) Trazodone Yohimbine (Yohimbe)
See also: Drugs for erectile dysfunction and premature ejaculation

v t e Phosphodiesterase inhibitors
PDE1	MMPX SCH-51866 Vinpocetine
PDE2	BAY 60-7550 Carbazeran EHNA Oxindole PDP
PDE3	Adibendan Amrinone (inamrinone) Anagrelide Benafentrine Bucladesine Carbazeran Cilostamide Cilostazol Enoximone Ensifentrine Imazodan KMUP-1 Meribendan Milrinone Olprinone Parogrelil Pimobendan Pumafentrine Quazinone RPL-554 Siguazodan Trequinsin Vesnarinone Zardaverine
PDE4	Apremilast Arofylline Atizoram Benafentrine Catramilast CC-1088 CDP-840 CGH-2466 Cilomilast Cipamfylline Crisaborole Denbutylline Difamilast Drotaverine Ensifentrine Etazolate Filaminast Glaucine HT-0712 ICI-63197 Indimilast Irsogladine Lavamilast Lirimilast Lotamilast Luteolin Mesembrenone Mesembrine Mesopram Oglemilast Piclamilast Pumafentrine Revamilast Ro 20-1724 Roflumilast Rolipram Ronomilast RPL-554 RS-25344 Tetomilast Tofimilast YM-976 Zardaverine
PDE5	Acetildenafil Aildenafil Avanafil Beminafil Benzamidenafil Dasantafil Icariin Gisadenafil Homosildenafil Lodenafil Mirodenafil MY-5445 Nitrosoprodenafil Norcarbodenafil SCH-51866 Sildenafil Sulfoaildenafil T-0156 Tadalafil Udenafil Vardenafil
PDE7	BRL-50481
PDE9	BAY 73-6691 PF-04447943 Paraxanthine
PDE10	Balipodect Mardepodect MK-8189 Papaverine TC-E 5005 Tofisopam
PDE11	BC11-38
Non-selective	Aminophylline Caffeine Choline theophyllinate CPX Dipyridamole Doxofylline Enprofylline Ibudilast IBMX Luteolin Pentoxifylline Propentofylline Theobromine Theophylline Zaprinast
Unsorted	Diazepam Diprophylline DPCPX Furafylline Lisofylline MDL-12330A Moxaverine Oxagrelate Pentifylline Proxyphylline Quercetin Satigrel Tolafentrine Trapidil
See also: Receptor/signaling modulators

Read other articles:

List of geothermal power stations in the United States

The Sonoma Calpine 3 geothermal power station of The Geysers in California. Main article: Geothermal energy in the United States Geothermal power stations in the United States are located exclusively within the Western United States where geothermal energy potential is highest. The highest concentrations are located in the Mayacamas Mountains and Imperial Valley of California, as well as in Western Nevada. The Geysers, a complex of 22 geothermal power stations located in Sonoma and Lake coun...

Ertholmene

ErtholmenePeta ErtholmeneLokasi Ertholmene di DenmarkGeografiLokasiLaut BaltikKoordinat55°19′12″N 15°11′16″E / 55.32000°N 15.18778°E / 55.32000; 15.18778Koordinat: 55°19′12″N 15°11′16″E / 55.32000°N 15.18778°E / 55.32000; 15.18778PemerintahanNegaraDenmark Fæstningen Christiansø Timur laut dari Bornholm, Denmark Lille Tårn (Menara kecil) di Frederiksø Jenis Benteng angkatan laut Dibangun 1684 Digunakan 1684–1855 (186...

Distrik Tel Aviv

Distrik Tel AvivTranskripsi - • Hebrewמחוז תל אביב • Arabic{{{arname}}}Cities10Local Councils2Regional Councils0CapitalTel AvivLuas • Total176 km2 (68 sq mi)Populasi (30.06.2008) • Total1.221.600 Distrik Tel Aviv (Ibrani: מחוז תל אביבcode: he is deprecated ) ialah salah satu 6 distrik di Israel dan termasuk kota berikut: Bat Yam בת ים Bnei Brak בני ברק Givatayim גבעתיים Herzliya הר�...

Ultimate Marvel vs. Capcom 3

Crossover fighting video game 2011 video gameUltimate Marvel vs. Capcom 3Front cover art, designed by Shinkiro, featuring several playable characters from the game.Developer(s)CapcomEightingPublisher(s)CapcomDirector(s)Hiroyuki NaraGo UsumaProducer(s)Ryota NiitsumaArtist(s)Takuro FuseComposer(s)Hideyuki FukasawaSeriesMarvel vs. CapcomEngineMT FrameworkPlatform(s)PlayStation 3Xbox 360PlayStation VitaPlayStation 4WindowsXbox OneReleasePlayStation 3, Xbox 360NA: November 15, 2011JP: November 17,...

Pemilihan umum Presiden Amerika Serikat di Oklahoma 1952

Pemilihan umum Presiden Amerika Serikat di Oklahoma 1952194819564 November 1952[1]8 suara elektor OklahomaKandidat Calon Dwight D. Eisenhower Adlai Stevenson Partai Republik Demokrat Negara bagian New York[2] Illinois Pendamping Richard Nixon John Sparkman Suara elektoral 8 0 Suara rakyat 518.045 430.939 Persentase 54,59% 45,41% Presiden petahanaHarry S. Truman Demokrat Presiden terpilih Dwight D. Eisenhower Republik Pemilihan umum Presiden Amerika Serik...

International House, Sydney

Historic site in New South Wales, AustraliaInternational HouseInternational House, 14-16 York Street, SydneyLocation14-16 York Street, Sydney central business district, City of Sydney, New South Wales, AustraliaCoordinates33°52′04″S 151°12′22″E / 33.8678°S 151.2062°E / -33.8678; 151.2062Built1913Built forEstate of the late Jeremiah Brice RundleArchitectRobertson & MarksArchitectural style(s)Federation Free Classical New South Wales Heritage RegisterOff...

WMGR

Radio station in Bainbridge, GeorgiaWMGRBainbridge, GeorgiaBroadcast areaTallahassee areaFrequency930 kHzBranding99.3 Contemporary Christian FavoritesProgrammingFormatContemporary ChristianAffiliationsWestwood OneOwnershipOwnerKevin Dowdy(Flint Media Inc.)HistoryFirst air date1946Call sign meaningW Marvin Griffin RadioTechnical informationFacility ID52401ClassBPower5,000 watts day500 watts nightTransmitter coordinates30°54′25.00″N 84°33′0.00″W / 30.9069444°N 84.5500...

大字 (数字)

この項目には、一部のコンピュータや閲覧ソフトで表示できない文字が含まれています（詳細）。数字の大字（だいじ）は、漢数字の一種。通常用いる単純な字形の漢数字（小字）の代わりに同じ音の別の漢字を用いるものである。概要壱万円日本銀行券（「壱」が大字）弐千円日本銀行券（「弐」が大字）漢数字には「一」「二」「三」と続く小字と、「壱」「�...

Belvedere Vodka

Brand of Polish rye vodka For other uses, see Belvedere (disambiguation). Belvedere VodkaTypeVodkaManufacturerPolmos ŻyrardówCountry of origin PolandIntroduced1993Alcohol by volume 40%Proof (US)80Related productsList of vodkasWebsitewww.belvederevodka.com Belvedere Vodka is a brand of Polish rye vodka produced and distributed by LVMH.[1] It is named after Belweder, the Polish presidential palace in Warsaw, whose illustration appears on its bottles. It is produced in...

Quart

Unit of volume with different values For other uses, see Quart (disambiguation). Not to be confused with cord (unit). Quarts redirects here. For the mineral, see Quartz. QuartOne-quart milk jugs (top shelf); half-gallon (two-quart) milk jugs (bottom shelf)General informationUnit ofVolumeSymbolqtConversions (imperial) 1 imp qt in ...... is equal to ... SI-compatible units 1.13652 L US customary units ≈&#...

Slammiversary (2006)

2006 Total Nonstop Action Wrestling pay-per-view event Slammiversary (2006)Promotional poster featuring various TNA wrestlersPromotionTotal Nonstop Action WrestlingDateJune 18, 2006CityOrlando, FloridaVenueImpact ZoneAttendance900[1]Tagline(s)This is the OnePay-per-view chronology ← PreviousSacrifice Next →Victory Road Slammiversary chronology ← Previous2005 Next →2007 The 2006 Slammiversary was a professional wrestling pay-per-view (PPV) event produced by ...

Château-Gaillard (Amboise)

Pour les articles homonymes, voir Gaillard et Château-Gaillard. Château-Gaillard Amboise Château-Gaillard Type Résidence royale Architecte attribué à Giovanni Giocondo[note 1]Paysagiste : Pacello da Mercogliano Début construction 1496 Fin construction 1559 (remaniement de la façade du corps de logis par Charles de Guise-Lorraine) Propriétaire initial Charles VIII Destination initiale Domaine Royal Propriétaire actuel SCI Dom Pacello Protection Inscrit MH (1963, 2023) Coo...

MI Darul Ulum

MI Darul Ulum Beraim merupakan satuan pendidikan dasar berjenis Madrasah ibtidaiah yang berada di bawah naungan Yayasan Al-Ma'arif Beraim. Saat ini MI Darul Ulum Beraim dikepalai Anwar Musaddad, M.Pd. Artikel ini tidak memiliki referensi atau sumber tepercaya sehingga isinya tidak bisa dipastikan. Tolong bantu perbaiki artikel ini dengan menambahkan referensi yang layak. Tulisan tanpa sumber dapat dipertanyakan dan dihapus sewaktu-waktu.Cari sumber: MI Darul Ulum – berita...

مطبخ فلسطيني

مطبخ فلسطينيمعلومات عامةالبلد / المنطقة دولة فلسطين النوع مطبخ وطني الثقافة ثقافة فلسطين تعديل - تعديل مصدري - تعديل ويكي بيانات جزء من سلسلة مقالات حولالمطبخ العربي حسب البلد الجزيرة العربية البحرين الإمارات الكويت سلطنة عمان قطر السعودية اليمن المغرب الكبير الجزائر ليب...

Генерал-майор

Генерал-майор Країна УкраїнаВид збройних сил СВ ЗСУ та ДШВ ЗСУ Повітряні сили ЗСУСили спеціальних операцій ЗСУЗвання не-НАТО OF-7Категорія вищий офіцерський складСтворено 1991Вище звання Генерал-лейтенантНижче звання Бригадний генералРівноцінні звання ВМС: Конт...

لبيد العبيدي

لبيد العبيدي معلومات شخصية الميلاد سنة 1937 بغداد تاريخ الوفاة سنة 2012 (74–75 سنة) مواطنة العراق الحياة العملية المدرسة الأم جامعة بغدادجامعة مانشستر المهنة كاتب بوابة الأدب تعديل مصدري - تعديل لبيد إبراهيم أحمد العبيدي (من مواليد 1937 - بغداد، توفي 5 آب/...

تصميم وتقانة

هذه المقالة يتيمة إذ تصل إليها مقالات أخرى قليلة جدًا. فضلًا، ساعد بإضافة وصلة إليها في مقالات متعلقة بها. (سبتمبر 2020) التصميم والتقانة مادة دراسية تُدرَس في جميع المراحل الابتدائية والمتوسطة في إنجلترا، ويدرسها الأطفال للتطوير في هذا المجال وصقل مهاراتهم في التقنية والتص...

Southwest Cay

Island of the Spratly Islands This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed.Find sources: Southwest Cay – news · newspapers · books · scholar · JSTOR (June 2011) (Learn how and when to remove this message) This article is about the island in the South China Sea. For the islet in the Caribbean Sea, see Serrana Bank. Puga...

Mauritz Eriksson

Swedish sport shooter Mauritz ErikssonEriksson (standing) at the 1920 Summer OlympicsPersonal informationFull nameAxel Mauritz ErikssonBorn(1888-12-18)18 December 1888Stockholm, SwedenDied14 February 1947(1947-02-14) (aged 58)Stockholm, SwedenSportSportSports shooting Medal record Men's shooting Representing Sweden Olympic Games 1912 Stockholm Team free rifle 1920 Antwerp 600 metre military rifle, prone 1912 Stockholm Team military rifle 1920 Antwerp Team 300 m military rifle,...

Fa (nota)

Questa voce o sezione sull'argomento teoria musicale non cita le fonti necessarie o quelle presenti sono insufficienti. Puoi migliorare questa voce aggiungendo citazioni da fonti attendibili secondo le linee guida sull'uso delle fonti. Note musicali V · D · M do · re · mi · fa · sol · la · si · (ut) Il fa è una nota musicale della scala diatonica fondamentale (l'unica scala priva di diesis e di bemolle, nei suoi diversi se...

Nitrosoprodenafil

See also

References

Read other articles: